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Holiday Rentals and Homes in Cummington, MA

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    All 23 Rentals in the Cummington Area
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    The following rentals are within 25 kilometers of Cummington, Hampshire County, Massachusetts.

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    €108
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    1 / 13
    5 of 5 stars (8) Excellent
    Becket, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    €127
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    1 / 16
    5 of 5 stars (9) Excellent
    Becket, MA
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    €193
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    1 / 23
    4.5 of 5 stars (16) Very good
    Plainfield
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    €455
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    1 / 11
    5 of 5 stars (9) Excellent
    Shelburne Falls, MA
    7 Bedrooms / 3 Bathrooms / Sleeps 14
    traveller have booked this property
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Our 7 bedroom, 3 bath, redone Federal House is the perfect place for family celebrations, school reunions, wellness, writing, quilting or other special interest gatherings. Your whole group can share our dining area and even enjoy the services of a gourmet chef should you desire. We have 8 quiet... View all property information
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    Location Information
    Shelburne Falls, Massachusetts 01370
    5 of 5 stars Reviewed 3 January 2014
    I stayed in this house with a group of about 14 friends from college (we're a few years out) the weekend after Christmas, and we had a great time staying at Susan's place in...
    5 of 5 stars Reviewed 3 July 2012
    The home was so perfect. Just a short walk to the center of Shelburne Falls, 5 minute drive to rafting outfitters, swimming holes. Huge house with a great kitchen, but you'll...
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    1 / 32
    5 of 5 stars (1) Excellent
    Becket, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 29 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    €123
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    1 / 22
    5 of 5 stars (5) Excellent
    Hawley, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Hawley, Massachusetts 01339
    5 of 5 stars Reviewed 12 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...
    5 of 5 stars Reviewed 21 August 2014
    Found this property to be a good one for the three of us. Great price, owner nearby and accessible. Very clean and comfy. Would have appreciated a little more about directions to...
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    €91
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    1 / 9
    5 of 5 stars (4) Excellent
    Conway, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The House in Pumpkin Hollow Bed and Breakfast is nestled in the foothills of the Berkshires in Conway, Masschusetts. It is surrounded by woods. fields, and other historic homes. Ideally situated 6 miles off Route 9, it is close to Northampton, Deerfield, Brattleboro, Amherst and Shelburne Falls.... View all property information
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    Location Information
    Conway, Massachusetts 01341
    4 of 5 stars Reviewed 30 August 2014
    I travel once a year to various interesting destinations with a best friend and this year we chose this Bed and Breakfast for its proximity to the Berkshires for hiking as well as...
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    €109
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    1 / 36
    5 of 5 stars (111) Excellent
    Charlemont, MA
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (111) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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    Location Information
    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed 23 May 2015
    I was relaxed on this vacation, because I didn't have to leave my pet in a kennel. We were able to go out without our dog to dinner and the owner even offered to check him if...
    5 of 5 stars Reviewed 13 May 2015
    Pat is such a friendly hostess, especially to 4 legged guests! While Tim and I enjoyed the peace and quiet, Mac, my 5 year old cocker spaniel had the time of his life! He played...
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    €178
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    1 / 16
    Becket, MA
    4 Bedrooms / 5 Bathrooms / Sleeps 12
    traveller have booked this property
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    Amenities & Details
    • Balcony
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • 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. Near Center pond where there are many boating... View all property information
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    Location Information
    Becket, Berkshires 01223
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    €455
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    1 / 18
    Hinsdale, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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    Location Information
    Hinsdale, Berkshires 01235
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    From
    €774
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    1 / 6
    Becket, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Becket, Berkshires 01223
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    €127
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    1 / 11
    Hinsdale, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Hinsdale, Berkshires 01235
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    €182
    / Night
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    1 / 19
    Cheshire, MA
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Mountain Views
    • Ping Pong Table
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Cheshire, Berkshires 01225
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    €956
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    1 / 9
    Becket, MA
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout... View all property information
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    Location Information
    Becket, Berkshires 01223
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    €319
    / Night
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    1 / 16
    Becket, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and... View all property information
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    Location Information
    Becket, Berkshires 01226
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    €273
    / Night
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    1 / 12
    Washington, MA
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
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    Location Information
    Washington, Massachusetts 01223
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    €464
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    1 / 27
    Williamsburg
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Mountain Views
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest... View all property information
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    Location Information
    Williamsburg, Hampshire County 01096
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    €182
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    1 / 6
    Savoy, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Savoy, Berkshires 01256
    From
    €128
    / Night
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    1 / 11
    Conway, MA
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Safe
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study 'nook', private bath with laundry facilities and a separate entrance. Guests are greeted every morning by two friendly... View all property information
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    Location Information
    Conway, Massachusetts 01341
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    €159
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    1 / 12
    Windsor, MA
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
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    Location Information
    Windsor, Berkshires 01270
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    From
    €393
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    1 / 8
    Charlemont, MA
    5 Bedrooms / 3 Bathrooms / Sleeps 14
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Charlemont, Berkshires 01339
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    €273
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    1 / 16
    Becket, MA
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Becket, Berkshires 01223
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    €1,502
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    1 / 10
    Becket, MA
    6 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Becket, Berkshires 01223