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 Rentals in Plainfield, MA

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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    ₹ 0
    ₹ 16,271 Average
    ₹ 67,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Plainfield area holiday home. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 24
    4.5 of 5 stars (16) Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection

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

    1 / 18
    5 of 5 stars (11) Excellent
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 16
    Becket, MA
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    1 / 37
    5 of 5 stars (139) Excellent
    Charlemont, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    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
    • Child-friendly
    • Smoking allowed
    • x
    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 the... View all property information
    Location Information
    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed 30 May 2016
    We really enjoyed our long weekend at the Cavalier Cottage in Charlemont MA. Patricia did everything possible to make our stay delightful and the homemade scones each morning were...
    5 of 5 stars Reviewed 23 April 2016
    It was wonderful to stay where our dog, Shima, was welcomed and considered an honored guest. There was a bowl for water on the kitchen floor and a cookie jar full of dog biscuits...
    See all reviews
    1 / 13
    5 of 5 stars (8) Excellent
    Becket, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed 3 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
    1 / 32
    5 of 5 stars (3) Excellent
    Becket, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars 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...
    5 of 5 stars Reviewed 19 August 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    See all reviews
    Charlemont, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Charlemont, Berkshires 01339
    1 / 11
    5 of 5 stars (9) Excellent
    Shelburne Falls, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    5 of 5 stars 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...
    5 of 5 stars 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...
    See all reviews
    Cheshire, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Cheshire, Berkshires 01225
    Dalton, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    Conway, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Nice to rent Cape Cod, Massachusetts .Here is the address apartment : 660 Washington Street, Theatre District, Boston, MA 02111 .Theare are two flats on same floorand the two street-facing sunny suites share an inside chill-out garden that is warmly and exquisitely decorated to provide our guests... View all property information
    Location Information
    Conway, Massachusetts 02111
    1 / 6
    5 of 5 stars (3) Excellent
    Savoy, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Savoy, Berkshires 01256
    5 of 5 stars Reviewed 4 February 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...
    5 of 5 stars Reviewed 9 December 2015
    Words can't begin to describe how amazing this rental is! My husband and I were married in November of 2014. Being a teacher, we couldn't go away for a long honeymoon so we...
    See all reviews
    Conway, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Conway, Massachusetts 01341
    1 / 22
    5 of 5 stars (6) Excellent
    Hawley, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    5 of 5 stars 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...
    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...
    See all reviews
    Becket, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Balcony
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Becket, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Garden
    • DVD Player
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223
    Hinsdale, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Parking
    • Shared Garden
    • Central Heating
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Hinsdale, Berkshires 01235
    Becket, MA
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Terrace
    • Balcony
    • Private Garden
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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.<BR>Near Center pond where there are many boating... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 11
    Becket, MA
    6 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Porch
    • Patio
    • Internet Access
    • Parking
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Becket, Berkshires 01223