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.

Williamsburg Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
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
    $259 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Williamsburg area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Williamsburg
    Sort by:
    Default
    The following rentals are within 30 kilometres of Williamsburg.
    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
    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
    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
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in the summer. The rear window...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Flight's End-A Country Home with Babbling Brook1 / 22
    (9)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
    • Cable/satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We needed a much needed break from the hustle and bustle of the city and we found the perfect place. Flight’s End was secluded, had a lot of empty space for our four legged...
    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...
    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
    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)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
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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 26 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!
    See all reviews
    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
    Holiday Rental House - 2 Bedrooms, 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
    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
    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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...
    See all reviews
    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
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
    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 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 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
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and...
    View all property information
    Location Information
    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Save time - get the best Williamsburg rentals sent straight to your email!
    Get the List
    Unique People & Pet-Welcoming Country Haven1 / 37
    (164)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
    • Cable/satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Beautiful, comfortable apartment with private entrance, in the country/woods but only a few minutes drive to Shelburne Falls village and bridge of flowers . Nice combination...
    Reviewed 15 October 2017
    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...
    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
    Big Sky Hilltop Sunset Room1 / 10
    (3)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This sublime rural setting is a peaceful haven. The sunrises and sunsets are breathtaking. I so enjoyed being there and look forward to coming back! Just minutes from Amherst...
    Reviewed 8 October 2017
    Reviewed 1 week agoThe Best B&B Experience ever!My boy friend and I had the good fortune to discover Big Sky Hilltop B&B this past week. It easily is the best B&B...
    See all reviews
    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Becket, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/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
    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
    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
    BigSkyHilltop Westerly Room1 / 8
    (1)Excellent
    Belchertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2016
    Our second two-night stay at Big Sky Hill Top was just as great as the first! This really is a BnB style rental: a great breakfast was included. They really go out of their way...
    See all reviews
    About this property
    Only 10 minutes from Amherst Center but almost 1000 feet above it and with a view for 60 miles, BigSkyHilltop is convenient to the 5 colleges, but a country gettaway looking out over the pastures of our neighbor's alpacas and donkeys with the forests and the Holyoke Hills beyond. Comfortable,...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located directly across the private...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Huntington
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You and your travel companions will be stricken by colonial beauty as you cross the threshold into this Huntington vacation rental home. The 3-bedroom, 2-bathroom house was constructed in 1789 and still boasts many of the original furnishings, but now features all of the modern amenities you'd...
    View all property information
    Location Information
    Huntington, Hampshire County 01050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    new condo with open floor plan and first floor master with view across the Connecticut River to Mount Holyoke. Quartz countertops and high end appliances make it a dream kitchen. Master bedroom has steam shower and soaking tub. Second floor has one single bedroom (with room for inflatable bed or...
    View all property information
    Location Information
    Hatfield, Hampshire County 01038
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Greenfield, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brandt House is a three-and-a-half-acre, turn-of-the-century estate located in a charming residential area of Greenfield, just minutes from I-91 and Route 2 in northwestern Massachusetts. Walking distance to downtown Greenfield and in the northern Pioneer Valley where culture, history, adventure,...
    View all property information
    Location Information
    Greenfield, Massachusetts 01301
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an antique desk that once housed...
    View all property information
    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    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. 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
    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
    • Cable/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
    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful turn-of-the-century Victorian is the former rectory to a beautiful old church that is now an artist studio (The Artist Common - available for rent separately). It is secluded a top a hill on 4 1/2 acres and has soaring ceilings, period details, modern kitchen and 2 1/2 bathrooms. You...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Holiday Rental House - 6 Bedrooms, 3 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
    • Cable/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
    Belchertown
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning 5,000-square-foot Tudor-style vacation rental home sits on 9 acres of professionally landscaped private property, ensuring an unforgettable Massachusetts retreat. Four bedrooms and 2.5 bathrooms comfortably accommodates 8 guests, with additional sleeping arrangements for up to 15 and...
    View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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
    List your property
    Owner log in