We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals and Homes in Windsor, MA

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    €0
    €181 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 25 kilometers of Windsor, Massachusetts.

    1 / 18
    5 of 5 stars (11) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 37
    5 of 5 stars (139) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 10
    5 of 5 stars (14) Excellent
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 24
    4.5 of 5 stars (16) Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country... View all property information
    Location Information
    Plainfield, Hampshire County 01070
    3 of 5 stars Reviewed 25 August 2014
    The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
    5 of 5 stars Reviewed 29 May 2014
    We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
    See all reviews
    1 / 16
    Becket
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 3 November 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed 28 June 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
    See all reviews
    1 / 8
    4 of 5 stars (2) Very good
    Pittsfield
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
    Location Information
    Pittsfield, Berkshires 01201
    3 of 5 stars Reviewed 17 August 2015
    The place was less than ideal in that the room smelled of smoke when we walked in. The bedroom had no windows and that felt very claustrophobic. It did have a kitchen which was...
    5 of 5 stars Reviewed 3 July 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
    See all reviews
    1 / 32
    5 of 5 stars (3) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 14 May 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
    5 of 5 stars Reviewed 19 August 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    See all reviews
    1 / 6
    5 of 5 stars (3) Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
    Location Information
    Savoy, Berkshires 01256
    5 of 5 stars Reviewed 3 February 2016
    What a quaint and absolutely lovely place to have spent the weekend. The quiet and peaceful surroundings along with the gorgeous wood interior made for a very homey and...
    5 of 5 stars Reviewed 9 December 2015
    Words can't begin to describe how amazing this rental is! My husband and I were married in November of 2014. Being a teacher, we couldn't go away for a long honeymoon so we...
    See all reviews
    Cheshire
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study,... View all property information
    Location Information
    Cheshire, Berkshires 01225
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 20
    5 of 5 stars (2) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
    Location Information
    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed 31 May 2016
    This home is meticulous, charming, cozy, comfortable and relaxing. We thoroughly enjoyed the backyard and spent hours just visiting with each other over a warm fire while the...
    5 of 5 stars Reviewed 29 November 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
    See all reviews
    1 / 25
    5 of 5 stars (9) Excellent
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, Hancock Shaker Village, Tanglewood, and MassMOCA. Home offers 3 bedrooms and 2 full baths with finished basement recreation room. Updated kitchen with all amenities needed for home... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 4 weeks ago
    This was a perfect weekend retreat for our extended family of six (three adult couples). The house is very warm and inviting, clean, and well-equipped. The surrounding woods and...
    5 of 5 stars Reviewed 7 July 2015
    My eight year old daughter and I had a wonderful time staying in Hancock. We were joined at different times by young cousins and grandparents - the kids loved the inside (the bunk...
    See all reviews
    Pittsfield
    7 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Patio
    • Hot Tub
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully... View all property information
    Location Information
    Pittsfield, Berkshires 01201
    1 / 19
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Hot Tub
    • Washer
    • Terrace
    • Shared Indoor Pool
    • Mountain Views
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 9 September 2015
    The units are clean and spacious and well stocked. Movie theater, swimming pools, outdoor picnic area with grills. and the mountain adjacent has plenty of outdoor activities...
    See all reviews
    1 / 18
    4.5 of 5 stars (9) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Skiing: Property Is...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Sauna
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Wyndham Bentley Brook Rental includes: King bed master, 2 doubles in the 2nd bedroom, queen sleep sofa, full living room, dining room and kitchen with utensils. New York + New Jersey Flock to Hancock Mass/Jiminy Peak Ski Area, rated Top 5 Family Mountains in the Northeast! Wyndham Bentley Brook... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 23 March 2015
    This is such a great property. We had a one bedroom unit which was still sufficient for 2 adults and 3 teens. Gorgeous large double bedroom with full bath and murphy bed and...
    4 of 5 stars Reviewed 26 January 2015
    Always a great trip for Friends and family. Easy quick park and party. They have a movie theater activities for kids all day long indoor outdoor swimming pool hot cider coffee and...
    See all reviews
    1 / 16
    4.5 of 5 stars (2) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 5 September 2015
    Great location near all outdoor activities including hiking, biking, golf and water sports. Rooms were spacious with 3 TVs. Wi-Fi was fast. One of the poops was heated. Owner...
    4 of 5 stars Reviewed 25 October 2014
    Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
    See all reviews
    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 18 February 2016
    My family and I come here every February to snowboard/ski. My boys are in their 20's and they still want to come here with the family and have fun. This year though my husband...
    See all reviews
    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Waterfront
    • Porch
    • Mountain Views
    • Central Heating
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
    Location Information
    North Adams, Berkshires 01247
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
    Location Information
    Hancock, Berkshires 01237
    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
    Location Information
    Hancock, Berkshires 01237
    5 of 5 stars Reviewed 30 July 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    See all reviews
    Get the List
    1 / 22
    5 of 5 stars (6) Excellent
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not... View all property information
    Location Information
    Hawley, Massachusetts 01339
    5 of 5 stars Reviewed 27 August 2015
    Very pleasant place to stay. Felt like staying at Grandma's house in the country. The owner is a very pleasant and easy going fellow and the price is reasonable. House and...
    5 of 5 stars Reviewed 11 September 2014
    The house was very clean and cozy. Everything was as shown in the pictures. As my friends and I are from the city, we love how quiet the area is. BBQ grill and bonfire were the...
    See all reviews
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Private Indoor Pool
    • Sauna
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Discover an unparalleled vacation destination at Wyndham Bentley Brook. This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal activities, return to your... View all property information
    Location Information
    Hancock, Berkshires 01237
    Charlemont
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
    Location Information
    Charlemont, Berkshires 01339
    Becket
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Balcony
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Beautifully appointed and immaculate 5,000 sq. ft. Becket Woods Contemporary sleeps 12 and is the perfect retreat for family and friends. The magnificent main level open floor plan is flooded with natural light and includes: • Romantic master bedroom suite, with its own deck, king bed, large... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 10
    5 of 5 stars (2) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is...
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master... View all property information
    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 11 September 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    5 of 5 stars Reviewed 6 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
    See all reviews
    1 / 14
    4.5 of 5 stars (3) Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    • Satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
    Location Information
    Hancock, Berkshires 001237
    Dalton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This home is an exact replica of the first Colonial ever built in Massachusetts back in the 1600's. It is called the "Parson Capens Home" and is located in Topsfield Mass. It has the design of the old but all the modern features. The home is nestled in the mountains of Berkshire County which have... View all property information
    Location Information
    Dalton, Berkshires 01226
    1 / 7
    5 of 5 stars (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Parking
    • Outdoor Dining Area
    • Grill
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of... View all property information
    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed 25 August 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    5 of 5 stars Reviewed 24 August 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in the...
    See all reviews
    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is...
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a... View all property information
    Location Information
    North Adams, Berkshires 01247
    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
    Location Information
    Hancock, Berkshires 01237
    4 of 5 stars Reviewed 11 August 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
    See all reviews
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Garden
    • DVD Player
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
    Location Information
    Becket, Berkshires 01223
    Hancock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor... View all property information
    Location Information
    Hancock, Berkshires 01237
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. PLEASE INQUIRE ABOUT DATES AND PRICE PRIOR TO SUBMITTING PAYMENT*** Bentley Brook, located in the Jiminy Peak ski area, offers a variety of on-site amenities -- from downhill skiing to swimming and biking. The Berkshire area also provides... View all property information
    Location Information
    Hancock, Berkshires 01237
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    • DVD Player
    • Mountain Views
    • Washer
    • Hot Tub
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new... View all property information
    Location Information
    Lanesboro, Berkshires 01224
    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Parking
    • Shared Garden
    • Central Heating
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
    Location Information
    Hinsdale, Berkshires 01235
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Mountain Views
    • Patio
    • Grill
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! This excellent property carries an abundance of amenities to make your northeast vacation one you’ll always cherish. Nestled along the scenic border of New York and... View all property information
    Location Information
    Hancock, Berkshires 01237
    North Adams
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Air Conditioning
    • Patio
    • Mountain Views
    • Grill
    • Porch
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    I have a two bedroom apartment and I am renting out the spare bedroom. It is at the end of a dead end street with a huge wooded backyard that includes a grill, picnic table and two fire pits. It's walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams.... View all property information
    Location Information
    North Adams, Berkshires 01247
    1 / 47
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Balcony
    • DVD Player
    • Terrace
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to our home! This beautiful, luxury unit is fully equipped with everything a family will need for the perfect Mountainside vacation. 3 Bedrooms accommodates 8 guests with all the comforts of home. Master bedroom, with Queen-size bed, wall mounted TV, large closet and a view of the... View all property information
    Location Information
    Pittsfield, Berkshires
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Terrace
    • Central Heating
    • DVD Player
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak (less than 5 minutes away) and to many cultural attractions of the Berkshires including Williamstown Theater Festival and Tanglewood. For outdoor lovers, Whitman Woods is near Mount Greylock Reservation, Audubon's... View all property information
    Location Information
    Hancock, Berkshires 01237
    Hancock
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Sauna
    • Patio
    • Balcony
    • Mountain Views
    • Hot Tub
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Commanding a stunning view of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pool. Go hiking, biking, fishing or horseback riding around the property or enjoy the off site... View all property information
    Location Information
    Hancock, Berkshires 01267
    Becket
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Terrace
    • Balcony
    • Private Garden
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding.<BR>Near Center pond where there are many boating... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 11
    Becket
    6 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Porch
    • Patio
    • Internet Access
    • Parking
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
    Location Information
    Becket, Berkshires 01223