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Cummington Holiday Rentals

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    Don't let other travellers get your favourite Cummington area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Cummington
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    The Clearing - Quiet - Close To Nature1 / 24
    (33)Excellent
    Cummington
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of Cummington.
    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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    Hinsdale, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Serene Lakefront Cottage1 / 105
    (12)Excellent
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Waterfront
    • Parking
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
    Reviewed 1 September 2015
    My husband and I plus our two dogs recently took one last family vacation before our first son arrives later this year. We were looking for a private and peaceful place where we...
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    About this property
    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge...
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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (163)Excellent
    Charlemont, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Beautiful and Quiet! We brought our 50lb lab/pit mix and were made to feel right at home! This is a great spot, far enough away from it all yet close enough to enjoy tubing or...
    Reviewed 1 week ago
    A quaint little cottage tucked in the Mohawk Trail. We were welcomed with open arms and so was Chevy our (blue nose pitbull) old man. He enjoyed the smooth crisp bowl of cold...
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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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    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Retreat in the Woods1 / 6
    (6)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 23 July 2017
    My husband and I vacationed in the Berkshires to hike and visit the MA state parks. This home is conveniently located within a 30 min. drive to many state parks and hiking...
    Reviewed 19 July 2017
    Lovely home - the pictures don't fully do it justice! The house is shielded from the road and set in a small clearing, so it gets plenty of light and a pleasant breeze at night...
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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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    Savoy, Berkshires 01256
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Flight's End-A Country Home with Babbling Brook1 / 22
    (8)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 26 August 2017
    We booked Flight's End for our recent mini vacation and were extremely pleased. The house is definitely a place where people lived and grew old, and had a comfortable...
    Reviewed 19 July 2017
    We are a couple in our 80's whose grown kids and grandkids took turns making short visits. They especially enjoyed the chance to use the canoe and kayak on the pond. We...
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 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...
    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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    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
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    Dalton, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Lakefront Summer Vacation Cottages1 / 5
    (2)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 12 August 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 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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    Location Information
    Goshen, Hampshire County 01032
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)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 19 February 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 25 October 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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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Escape to the Berkshires!1 / 32
    (4)Excellent
    Becket, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 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 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...
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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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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Hawley, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Mountain Views
    • Central Heating
    • Parking
    • Private Garden
    • 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    Becket, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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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 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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    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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