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Holiday Rentals in Westfield

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    All 26 Rentals in Westfield
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    The following rentals are within 40 kilometers of Westfield.
    Serene Lakefront Cottage1 / 63
    (12)Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (11)Very good
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Escape to the Berkshires!1 / 32
    (4)Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    Granville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The rental was spacious, immaculate and very comfortable and it's situated in a very private and relaxing part of the forest.
    Reviewed 4 weeks ago
    Just what the doctor ordered. Beautiful, peaceful getaway in a lovely private community. Comfortable beds, great kitchen, would DEFINITELY stay again.
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    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the...
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    Granville, Berkshires 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bloomfield, CT
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEAUTIFUL 100% NEWLY renovated Victorian Mansion, on 3.5 acre private ESTATE., directly alongside the ELEGANT greens and fairways of the prestigious private TUMBLE BROOK COUNTRY CLUB. LARGE INGROUND SWIMMING POOL. Great GOLF COURSE views from every window. PRIVATE- AWAY FROM THE ROADS- Large,...
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    Bloomfield, Connecticut 06002
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful turn-of-the-century Victorian is the former rectory to a beautiful old church that is now an artist studio (The Artist Common - available for rent separately). It is secluded a top a hill on 4 1/2 acres and has soaring ceilings, period details, modern kitchen and 2 1/2 bathrooms. You...
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    Belchertown, Hampshire County 01007
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and...
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    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Corner Cottage in 16 Acres Springfield1 / 8
    (1)Excellent
    East Longmeadow
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2017
    peaceful and good host we would stay again and recommend her place to anyone also close to any stores
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    About this property
    Corner Cottage. This is a private house. It is a house-share. There are 2 adults and 2 cats living in the home. My home is very bright and sunny. My place is close to family-friendly activities, nightlife, and public transport. You’ll love my place because it is quiet and because of the location....
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    Location Information
    East Longmeadow, Massachusetts 01128
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    West Springfield
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lily's Lodge is your Home away from Home in Western Massachusetts. We are located directly across the street from the Eastern States Exposition Fairgrounds, minutes from downtown Springfield and within 5-15 minute drive to area colleges, Basketball Hall of Fame, and Six Flags. We provide our...
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    Location Information
    West Springfield, Massachusetts 01089
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    Starlight Llama - The White Room1 / 5
    (11)Excellent
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2017
    We had a great time in Northampton and then checked in. Gracious kind comfortable host let us leave our stuff recommended the most wonderful place for dinner. It was so quite...
    Reviewed 27 September 2016
    I enjoyed the adventure of getting here, the lovely owners, the excellent breakfast, the animals wandering around the property and hearing the coyotes at night from the comfort...
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    About this property
    The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in the summer. The rear window...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Big Sky Hilltop Sunset Room1 / 10
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2016
    What a lovely opportunity to meet these two gracious hosts. If/when I return to Amherst theirs will be the first lodging I look into. Morning coffee on the back deck watching...
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    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
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    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Barkhamsted, CT
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,...
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    Barkhamsted, Connecticut 06063
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    Becket
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Balcony
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    new condo with open floor plan and first floor master with view across the Connecticut River to Mount Holyoke. Quartz countertops and high end appliances make it a dream kitchen. Master bedroom has steam shower and soaking tub. Second floor has one single bedroom (with room for inflatable bed or...
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    Hatfield, Hampshire County 01038
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY...
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    Otis, Berkshires 01255
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Agawam
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit Agawam in comfort when you stay at this cozy vacation rental studio that sleeps 5, only a few minutes drive south from Springfield! Complete with a well-equipped kitchen, a plush queen-sized bed and a cozy lounge area with a flat-screen cable TV, this studio is perfect for families and...
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    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    Belchertown
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning 5,000-square-foot Tudor-style vacation rental home sits on 9 acres of professionally landscaped private property, ensuring an unforgettable Massachusetts retreat. Four bedrooms and 3 bathrooms comfortably accommodates 8 guests, with additional sleeping arrangements for up to 15 and...
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    Belchertown, Hampshire County 01007
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    BigSkyHilltop Westerly Room1 / 8
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 October 2016
    Our second two-night stay at Big Sky Hill Top was just as great as the first! This really is a BnB style rental: a great breakfast was included. They really go out of their way...
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    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
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    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Winsted, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake house totally rebuilt in 2016 to high standards. Very warm in cold months, central air in summer. Waterski in Summer, snow ski in winter at nearby local ski mountains (Sundown and Mohawk). Choice location on beautiful lake with full boating. Dockage for your boat directly in front of...
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    Winsted, Connecticut 06098
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Garden
    • DVD Player
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Becket
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Terrace
    • Balcony
    • Private Garden
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Starlight Llama - The Lavender Room1 / 8
    (11)Excellent
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    Our hosts were very friendly and helpful and our night was incredibly peaceful. When we returned from Northampton in the evening we understood why they include...
    Reviewed 1 November 2016
    We just returned from a 3-night stay at Starlight while in the Pioneer Valley for a family get-together and couldn't have been more pleased with the accommodations - and the...
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    About this property
    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located directly across the private...
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    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Starlight Llama - The Pink Room1 / 7
    (10)Excellent
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2017
    We stayed here for one night in the pink room. We really enjoyed our stay. The room has it's own bathroom. If you forget to bring toiletries,there is shampoo, body wash, lotion...
    Reviewed 28 June 2016
    Staying on the farm was amazing. If you are an animal lover, you will surely love this place! The owners were great, and even gave us a little tour of the property. Silent at...
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    About this property
    Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an antique desk that once housed...
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    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lakefront Summer Vacation Cottages1 / 5
    (2)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    A perfect start to our 3 week stay in Mass. Fantastic, quiet, lakeside location with warm water - so different from the UK! Full use of kayaks, canoe, paddleboard and raft...
    Reviewed 21 June 2017
    Very nice and quiet, clean and confortable. Kids enjoy Adults love it and i will say we will go back
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    About this property
    We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique and enjoyable! The property is...
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    Goshen, Hampshire County 01032
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Hartford, CT
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Sauna
    • Hot Tub
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house sits on 2.6 wooded acres, and there are a total of 9 rooms which includes: UPPER LEVEL: Four bedrooms, two baths, large dining room and kitchen overlooking mountain and deck, 32 inch TV, WiFi, and full kitchen awaiting the chef. There is a King bed in Master bedroom, a Queen in Guest...
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    Hartford, Connecticut 06019
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
    • Air Conditioning
    • Patio
    • Grill
    • Internet Access
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck with a patio set and grill, a...
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    Location Information
    Goshen, Hampshire County 01032
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 8
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