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.

Grafton 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
    $281 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Grafton area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 23 Rentals in Grafton
    Sort by:
    Default
    Log Cabin With Views1 / 13
    (5)Excellent
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Grafton
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Grafton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern 4-bedroom, 3-bathroom Vermont vacation rental home comfortably accommodates 8 guests in 3,800 square feet of luxury. The authentic, newly renovated 1950's farmhouse offers a quintessential homestead experience, nestled in the Green Mountains of Southern Vermont on stunning, lush...
    View all property information
    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    The following rentals are within 15 kilometres of Grafton.
    Charming and cozy Log cabin near Stratton Vermont1 / 12
    (1)Excellent
    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • Washer
    • Grill
    • Central Heating
    • Porch
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2016
    Absolutely enjoyed our stay here. It was in a great location and the house was very clean and comfortable. It had ample supplies for preparing meals in the kitchen. Only issue...
    See all reviews
    About this property
    Quaint and rustic log home, Very private. open floor with cathedral ceiling. Covered porch. Only 3 miles from Stratton Mountain entrance, and 15 minutes from Bromley Close to Manchester premium outlet stores. Golf, hiking, horseback riding, white water rafting are all within minutes from the...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Classic Vermont Farmhouse1 / 12
    (1)Excellent
    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Central Heating
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    Clean, cozy, comfortable. The house was a lot larger than we expected, as was the backyard. It sort of just opens up to a great view of a few peaks in the distance. There is a...
    See all reviews
    About this property
    CLASSIC VERMONT HILLTOP FARMHOUSE - 5 BEDROOMS SLEEP UP TO 12 PEOPLE. GREAT FOR FAMILY & GROUP GET TOGETHERS. SECLUDED, YET WITHIN 1 HOUR'S DRIVING DISTANCE TO 6 MAJOR SKI/RECREATIONAL AREAS – OKEMO IS 8 MILES AWAY. Private and secluded, yet less than 8 miles to the Okemo Mountain resort and...
    View all property information
    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
    Make Enquiry
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Amare Guesthouse is a relaxed and inviting recently restored Victorian home steps from downtown Chester VT. From coffee to cocktails relax on one of the large porches. Walking distance to restaurants and pubs, rivers, farms, trails, antique shops, galleries, and a grocery store.  Enjoy small...
    View all property information
    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Hugging Bear Inn - Tower Room1 / 10
    (1)Very good
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Air Conditioning
    • Terrace
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2015
    We stay in Vermont several times a year and this time we stayed at the Hugging Bear Innin Chester. Laura and her family are wonderful people and welcomed us into their home as...
    See all reviews
    About this property
    The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks the village green. Full Vermont...
    View all property information
    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Jamaica
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Washer
    • Mountain Views
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic and Serene. Sleeps a Family + Friends, Furry or Otherwise. Ski at Stratton, Bromley, Magic, Okemo and Mt.Snow Private Yoga Studio Welcome to our Jamaica farmhouse, a place with space to live and breathe the beauty that Vermont has to offer. Simple, authentic, and perfectly close to the...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    • DVD Player
    • Porch
    • Internet Access
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the...
    View all property information
    Location Information
    Chester, Vermont 05143
    Private Room - 6 Bedrooms, 7 Bathrooms, Sleeps 18
    Make Enquiry
    Save time - get the best Grafton rentals sent straight to your email!
    Get the List
    Vermont Farmhouse Rooms to share1 / 10
    (2)Excellent
    Chester
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2016
    Like your grandparents' old vacation home, full of funky furniture but comfortable and homey. The public areas are vast, with two dining areas seating 6-8 each and a living room...
    Reviewed 14 September 2016
    This was my first visit to the Okemo area in the summer (have skied several times) and I was looking for a place stay while I did some hiking and mountain biking. The farmhouse...
    See all reviews
    About this property
    We have a Classic Vermont Hillside Farmhouse. There are 5 bedrooms - all rooms can accommodate two people. One room has 2 twin beds AND a double, so 4 people could share that room. There are two full bathrooms in the house, a large kitchen, large dining room and living-room. There is also a...
    View all property information
    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Enquiry
    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Porch
    • Washer
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful 2-story log cabin with 3 bedrooms, 2 baths and hardwood floors throughout. The most prominent feature of the house is the large floor to ceiling fireplace that is perfect after a long day of skiing. Home has full internet access, with Direct TV and large flat screen TV. Has a large...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Porch
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared...
    View all property information
    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 1820 stone house, The Cairn, just off Rte 103 in a small village enclave reached by crossing the historic Bartonsville covered bridge- rebuilt after hurricane Irene. The house is surrounded by a lovely garden that reaches down to the Williams River in the back. The main floor has an open...
    View all property information
    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Andover
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are seeking to get away from the craziness of everyday life and take in natural beauty and the enjoyment of downhill and cross country skiing, snowshoeing, hiking, antique shopping, and cool resturants you found the right spot. Close to: Okemo, Bromley, Killington, Jackson Gore, and Magic...
    View all property information
    Location Information
    Andover, Vermont 05143
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bear Creek Condo just minutes from Stratton Mountain. Enjoy this newly remodeled condo with up to 12 of your friends/family. Two queen sized beds, two full sized bunk beds in the kids room. Large Screen TV in the Kids room and Family Room. Brand New Everything. Linens and Towels included for...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    Jamaica
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Garden
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home in a quiet area in the woods with magnificent views. An easy 10 minute ride to Stratton and other ski areas. Main floor of house includes master bedroom with king bed and bathroom suite including spa tub and stall shower. Fully stocked kitchen with eating kitchen as well as counter...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
    Make Enquiry
    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Mountain Views
    • Internet Access
    • Private Garden
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail) Close...
    View all property information
    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 1843 Stone House is a pre-civil war home that is quaint and comfortable for 2 families or 3 couples. The house is full of charm while also providing modern amenities. The Chester Village green is a short walk from the house where shops and restaurants are housed in buildings from yesteryear....
    View all property information
    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Balcony
    • Grill
    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Jamaica in all its year-round glory: Swim in the rivers, lakes, canoe, kayak, sail, hike to the water falls ,leaf-peep, shop, ski Stratton, snow-shoe, cross-country, kayak, sail, walk across the bridge to the State Park. Jamaica village is a stone's throw away by foot. Make our...
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Large, Lovely, Affordable Mountain Home1 / 20
    (3)Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2014
    First of all, I want to thank Mary for being very friendly in providing us with information and details on getting to their house. We (group of 7) did not get to meet them...
    See all reviews
    About this property
    The Windham Country House, a spacious contemporary home, sits on a secluded country road, providing you with peace, privacy and beautiful scenery, while being near many of southern Vermont's activities. GREAT ACCOMMODATIONS The Windham Country House has five large, lovely bedrooms and three full...
    View all property information
    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Jamaica
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Central Heating
    • Mountain Views
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular timberframe home. Quintessential Vermont experience. More ski lodge than house. The non-skiers will be very happy spending time here. A short 4-mile drive to the Stratton access road. (12 minutes door-to-door to the ski resort). One of the finest rental homes in Southern Vermont....
    View all property information
    Location Information
    Jamaica, Vermont 05343
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
    Make Enquiry
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Secure Parking
    • Porch
    • Internet Access
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our...
    View all property information
    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property
    Owner log in