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Cummington Vacation Rentals

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    Don't let other travelers get your favorite Cummington area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Cummington
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    Cummington
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 15 miles of Cummington.
    Serene Lakefront Cottage1 / 21
    (11)Excellent
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    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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    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed October 25, 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    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,...
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    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming Affordable  Home for groups up to 141 / 11
    (9)Excellent
    Shelburne Falls, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 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...
    Reviewed July 3, 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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    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...
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    Location Information
    Shelburne Falls, Massachusetts 01370
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    Retreat in the Woods1 / 6
    (4)Excellent
    Savoy, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 2017
    We stayed at this retreat in the woods and found it to be a perfect place for rest, relaxation, and recharging. The home is clean, modern, and sunlit, with a large kitchen that...
    Reviewed February 3, 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...
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    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...
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    Location Information
    Savoy, Berkshires 01256
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Becket, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    Location Information
    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Berkshire house w/ fireplace, A/C, WiFi & laundry1 / 27
    (16)Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 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...
    Reviewed May 29, 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...
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    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...
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    Location Information
    Plainfield, Hampshire County 01070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Hinsdale, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • DVD Player
    • Washer
    • Balcony
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hinsdale, Berkshires 01235
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Flight's End-A Country Home with Babbling Brook1 / 22
    (6)Excellent
    Hawley, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 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...
    Reviewed September 11, 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...
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    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...
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    Location Information
    Hawley, Massachusetts 01339
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cheshire, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    Cheshire, Berkshires 01225
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Conway, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • 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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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Porch
    • Patio
    • Grill
    • Satellite TV
    • Parking
    • DVD Player
    • Air Conditioning
    • Internet Access
    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 - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (156)Excellent
    Charlemont, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Traveler-friendly cancellation policy
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    Amenities & Details
    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Yard
    • Satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We had a wonderful, relaxing weekend. This cottage is nestled in the woods, but a short drive to civilization. If you travel with your dog...stay here!
    Reviewed 4 weeks ago
    I was playing for a nearby festival and was so pleased to find Cavalier Cottage. It can be very hard to find a pet-friendly, affordable, quiet place that will rent for a short 2...
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    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 area of Western Massachusetts with or without their companion animals. Now in its sixth year,...
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    Location Information
    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Test Listing - Do Not Rent1 / 4
    (2)Very good
    Hawley, MA
    1 Bedroom, 50 Bathrooms, Sleeps 50 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    What an experience-great expanse inside with lots of room to explore. All of our guests enjoyed the plethora of bathrooms the place had to offer. Minus one star for only having...
    Reviewed 4 weeks ago
    It is a pretend cave, but it is a nice pretend cave. I have never stayed in a cave with so many bathrooms. The best part is the location, though - there is a gold course o site...
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    About this property
    Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test...
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    Location Information
    Hawley, Massachusetts 01339
    Rental Home - 1 Bedroom, 50 Bathrooms, Sleeps 50
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    Lakefront Summer Vacation Cottages1 / 5
    (1)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    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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    Plainfield
    7 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Apartment/Flat, in Plainfield at Perry's, from 232 USD per night per person and 233 USD for 2! Discover Plainfield, and enjoy the advantages of staying at a locals': practical advice, a welcoming atmosphere and great prices. A Whole Lodging (for cottage, appartment, house), from 1 to 10 people. At...
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    Location Information
    Plainfield, Hampshire County 01070
    Condo/Apartment - 7 Bedrooms, 1 Bathroom, Sleeps 10
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    Dalton, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Dalton, Berkshires 01226
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Hawley, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Mountain Views
    • Central Heating
    • Parking
    • Private Yard
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Valley View is a charming one-bedroom house looking out over a large meadow from the top of a hill. The house features a wraparound deck which extends the living space into the outdoors, and large picture windows and sliding glass doors bring light and views inside. A woodstove in the living room...
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    Location Information
    Hawley, Massachusetts 01339
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Cummington Flight and Weather Info
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    37.8 miles from Cummington
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