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.

Holiday Homes and Apartments Cummington, MA and nearby

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.
dd/mm/yyyy dd/mm/yyyy
    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}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 23 Rentals in the Cummington Area
    loading...
    Don't let other travellers get your favourite Cummington area holiday rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 25 kilometres of Cummington, Hampshire County, Massachusetts.

    From
    $638
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (9) Excellent
    Shelburne Falls, MA
    7 Bedrooms / 3 Bathrooms / Sleeps 14
    traveller have booked this property
    Overview Reviews (9) Make Enquiry
    From
    $177
    / Night
    Payment Protection
    View Details
    1 / 16
    5 of 5 stars (9) Excellent
    Becket, MA
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travellers have booked this property
    Overview Reviews (9) Make Enquiry
    From
    $128
    / Night
    Payment Protection
    View Details
    1 / 9
    5 of 5 stars (4) Excellent
    Conway, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    From
    $126
    / Night
    Payment Protection
    View Details
    1 / 13
    5 of 5 stars (8) Excellent
    Becket, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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,... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 4 November 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed 29 June 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
    See all reviews
    From
    $351
    / Night
    Payment Protection
    View Details
    1 / 32
    5 of 5 stars (1) Excellent
    Becket, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 30 August 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
    See all reviews
    From
    $153
    / Night
    Payment Protection
    View Details
    1 / 36
    5 of 5 stars (108) Excellent
    Charlemont, MA
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (108) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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 and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 30 March 2015
    Beyond all expectations, we relaxed in royal blue, in quiet and comfortable surroundings -- a place to which we plan to return again, to enjoy in other seasons, to fully...
    5 of 5 stars Reviewed 24 March 2015
    This cottage is a great place to stay, especially for those traveling with pets. Pat is very hospitable and there is plenty of privacy. We definitely need more people & places...
    See all reviews
    From
    $172
    / Night
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (5) Excellent
    Hawley, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
    Make Enquiry
    Location Information
    Hawley, Massachusetts 01339
    5 of 5 stars Reviewed 12 September 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 the...
    5 of 5 stars Reviewed 21 August 2014
    Found this property to be a good one for the three of us. Great price, owner nearby and accessible. Very clean and comfy. Would have appreciated a little more about directions to...
    See all reviews
    From
    $223
    / Night
    Payment Protection
    View Details
    1 / 16
    Becket, MA
    4 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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. Near Center pond where there are many boating... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    From
    $638
    / Night
    Payment Protection
    View Details
    1 / 18
    Hinsdale, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
    Make Enquiry
    From
    $552
    / Night
    Payment Protection
    View Details
    1 / 8
    Charlemont, MA
    5 Bedrooms / 3 Bathrooms / Sleeps 14
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $255
    / Night
    Payment Protection
    View Details
    1 / 6
    Savoy, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    Location Information
    Savoy, Berkshires 01256
    From
    $1,085
    / Week
    Payment Protection
    View Details
    1 / 6
    Becket, MA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    From
    $383
    / Night
    Payment Protection
    View Details
    1 / 12
    Washington, MA
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Shingle style, timber frame, passive solar, Berkshie 'Cottage' Built along side of Coles Brook, the manor is a retreat destination any time of the year. The seclusion and tranquility of the custom built home and site are unique and comforting for family gatherings and weekend getaways. View all property information
    Make Enquiry
    From
    $179
    / Night
    Payment Protection
    View Details
    1 / 11
    Hinsdale, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
    Make Enquiry
    From
    $651
    / Night
    Payment Protection
    View Details
    1 / 27
    Williamsburg
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Mountain Views
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Flower Hill Farm Retreat is housed within a 1790 farmhouse and studio situated on an east facing hillside fifteen minutes west of Northampton, Massachusetts. You can rent the entire retreat or separate apartments. See Rates below in this write up. Rambling organic gardens, fields and forest... View all property information
    Make Enquiry
    From
    $447
    / Night
    Payment Protection
    View Details
    1 / 16
    Becket, MA
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01226
    From
    $383
    / Night
    View Details
    1 / 16
    Becket, MA
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    From
    $223
    / Night
    Payment Protection
    View Details
    1 / 12
    Windsor, MA
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
    Make Enquiry
    From
    $1,341
    / Week
    Payment Protection
    View Details
    1 / 9
    Becket, MA
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    From
    $180
    / Night
    Payment Protection
    View Details
    1 / 11
    Conway, MA
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Safe
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
    Make Enquiry
    Get the List
    From
    $2,107
    / Week
    View Details
    1 / 10
    Becket, MA
    6 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
    Make Enquiry
    Location Information
    Becket, Berkshires 01223
    From
    $255
    / Night
    Payment Protection
    View Details
    1 / 19
    Cheshire, MA
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Internet Access
    • Mountain Views
    • Ping Pong Table
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
    Make Enquiry
    From
    $271
    / Night
    Payment Protection
    View Details
    1 / 23
    4.5 of 5 stars (16) Very good
    Plainfield
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
    Make Enquiry
    3 of 5 stars Reviewed 26 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...
    5 of 5 stars 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