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Southampton Vacation Rentals

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    Don't let other travelers get your favorite Southampton area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Southampton
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    The following rentals are within 20 miles of Southampton.
    Serene Lakefront Cottage1 / 21
    (12)Excellent
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    NEW! Historic 3BR Huntington Home - Walk to River!1 / 25
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    Huntington
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (11)Very good
    Becket, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    new Condo close to Route 91, Northampton and Five Colleges1 / 13
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    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
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    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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    Escape to the Berkshires!1 / 32
    (4)Excellent
    Becket, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches &amp...
    Reviewed May 14, 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...
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    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...
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    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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 August 12, 2017
    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 June 21, 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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    Location Information
    Goshen, Hampshire County 01032
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Windy Top Stone Cottage1 / 12
    NEW!
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    North Granby, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Patio
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Windy Top Cottage is an old stone building constructed in 1935 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to “summer” in the early part of the 20th Century. The cottage was the place where the domestic staff stayed when...
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    North Granby, Connecticut 06060
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Starlight Llama - The White Room1 / 5
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    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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    Location Information
    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    NEW! Agawam Studio w/ Easy Access to Attractions1 / 24
    NEW!
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    Agawam, MA
    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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    Location Information
    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    Granville, MA
    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 July 25, 2017
    The rental was spacious, immaculate and very comfortable and it's situated in a very private and relaxing part of the forest.
    Reviewed July 25, 2017
    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 - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Becket, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Terrace
    • Balcony
    • Private Yard
    • 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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    Location Information
    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Lily's Lodge1 / 6
    NEW!
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    West Springfield, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • 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 Pink Room1 / 7
    NEW!
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Corner Cottage in 16 Acres Springfield1 / 8
    (1)Excellent
    East Longmeadow, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Satellite TV
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Starlight Llama - The Lavender Room1 / 8
    NEW!
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Becket, MA
    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Enjoy the beautiful Berkshires, the horses and the Otis Reservoir1 / 10
    NEW!
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    Otis, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Housekeeping Included
    • Parking
    • Satellite TV
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our accommodations are cozy and bright. The horses live right on the property and our dock is within walking distance from your getaway. This apartment has a queen bed in the bedroom and a pull out couch in the living room. The living room also has a trundle bed which can accommodate 2...
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    Otis, Berkshires 01253
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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 October 26, 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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    Big Sky Hilltop Sunset Room1 / 10
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 13, 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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    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    NEW! 4BR Belchertown Tudor Home on 9 Private Acres1 / 24
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    Belchertown
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Internet Access
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    • 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 2.5 bathrooms comfortably accommodates 8 guests, with additional sleeping arrangements for up to 15 and...
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    Belchertown, Hampshire County 01007
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Otis, MA
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Washer
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    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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    NEW! Peaceful 2BR Goshen Cabin w/Great Deck!1 / 24
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
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    • Patio
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    • Satellite TV
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    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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    Goshen, Hampshire County 01032
    Cabin - 2 Bedrooms, 1 Bathroom, 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
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    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
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Conway, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Conway, Massachusetts 01341
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    East Otis, MA
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    Location Information
    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    20.4 miles from Southampton
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