We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cummington Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $264 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Cummington area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Cummington
    Sort by:
    Default
    The following rentals are within 25 kilometres of Cummington.
    Serene Lakefront Cottage1 / 21
    (12)Excellent
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (11)Very good
    Becket, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Charming Affordable  Home for groups up to 141 / 11
    (9)Excellent
    Shelburne Falls, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Escape to the Berkshires!1 / 32
    (4)Excellent
    Becket, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 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 15 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...
    See all reviews
    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
    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Retreat in the Woods1 / 6
    (6)Excellent
    Savoy, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 4 weeks ago
    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...
    See all reviews
    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
    Location Information
    Savoy, Berkshires 01256
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Conway, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Conway, Massachusetts 01341
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Flight's End-A Country Home with Babbling Brook1 / 22
    (7)Very good
    Hawley, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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...
    Reviewed 27 August 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...
    See all reviews
    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
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Berkshire house w/ fireplace, A/C, WiFi & laundry1 / 27
    (16)Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 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 30 May 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...
    See all reviews
    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...
    View all property information
    Location Information
    Plainfield, Hampshire County 01070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Unique People & Pet-Welcoming Country Haven1 / 37
    (159)Excellent
    Charlemont, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Travellers' Choice
    Check in Check out
    Show Prices
    Payment Protection
    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 2 days ago
    Loved my stay at Cavalier Cottage! The decor is warm and cozy, with big windows up front that overlook the beautiful garden. In the mornings, I was treated to Patricia's...
    Reviewed 2 weeks ago
    We wanted to see the Berkshires area and chose Shelburne Falls for a couple of days. Having a Cavalier, I was drawn to Patricia's home. The accommodations were roomy and in a...
    See all reviews
    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,...
    View all property information
    Location Information
    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Hinsdale, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • DVD Player
    • Washer
    • Balcony
    • Wi-Fi
    • 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...
    View all property information
    Location Information
    Hinsdale, Berkshires 01235
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Save time - get the best Cummington rentals sent straight to your email!
    Get the List
    Cheshire, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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,...
    View all property information
    Location Information
    Cheshire, Berkshires 01225
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Dalton, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Dalton, Berkshires 01226
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    Becket, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Make Enquiry
    Plainfield
    7 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Plainfield, Hampshire County 01070
    Condo/Apartment - 7 Bedrooms, 1 Bathroom, Sleeps 10
    Make Enquiry
    Becket, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    Hawley, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Lakefront Summer Vacation Cottages1 / 5
    (2)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days 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 22 June 2017
    Very nice and quiet, clean and confortable. Kids enjoy Adults love it and i will say we will go back
    See all reviews
    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...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    List your property
    Owner log in