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Jamaica House Rentals

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    Don't let other travellers get your favourite Jamaica area holiday rental. You're so close to securing your perfect getaway. Book today.
    33 Matching Rentals in the Jamaica AreaView all 44 rentals
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    Charming and cozy Log cabin near Stratton Vermont1 / 12
    (1)Excellent
    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Jamaica
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • 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...
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    Jamaica, Vermont 05343
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Jamaica
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • 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....
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    Jamaica, Vermont 05343
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    Jamaica
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • 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...
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    Jamaica, Vermont 05343
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Jamaica
    2 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Washer
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book your next east coast vacation at this modern 2-bedroom, 2-bathroom vacation rental townhouse perfect for a family reunion. This spacious 1,400-square-foot property offers 12 lucky guests a clean and polished interior design, which features tall vaulted ceilings, a charming wood-burning stove,...
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    Jamaica, Vermont 05343
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 12
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    The following rentals are within 15 kilometres of Jamaica.
    Beautiful Vacation Home at Strattonwald at Stratton Mountain1 / 18
    (6)Excellent
    Stratton Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    Wonderful, spacious, warm, & inviting! 5 minute drive to Stratton. We would definatey go back! Comfortable beds, fully stocked kitchen! Nice large dining table.
    Reviewed 19 February 2018
    We really enjoyed our stay at Midge's beautiful ski house. Great location...Stratton is 5 minutes up the road and Manchester 10-15 mins away. We did expect a mountain shuttle...
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    About this property
    Beautiful vacation home at Strattonwald at Stratton Mountain. Free shuttle picks you up at the end of our driveway and delivers you to Stratton's base lodge. The house accommodates up to 6 adults and four children in four bedrooms: kids room with bunk, trundle and full size bed, two queen bedrooms...
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    Stratton Mountain, Vermont 05340
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Kassmel's Mountain Haus1 / 11
    (1)Very good
    West Wardsboro
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Central Heating
    • Grill
    • Cable/satellite TV
    • Parking
    • DVD Player
    • Hot Tub
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 January 2018
    It is a beautiful house with wood burning fireplace and hot tub with convient distance to Mount Snow. The kitchen was well stocked with appliances, pots/pans and basics as well...
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    About this property
    Our home is nestled in the Green Mountains in Snow Mountain Farms midway between Mt. Snow and Stratton Mountains. Located on 2 acres, our ranch style home has a fully equipped kitchen, washer/dryer, skylights, Satellite TV, DVD, stereo/CD, wood burning fireplace (wood provided) wrap around deck...
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    West Wardsboro, Vermont 05355
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family-friendly cabin with a deck, excellent home base for skiing1 / 27
    (1)Excellent
    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2018
    Our stay at the Sherwood Escape was exactly what we expected. Our group included 2 families (4 adults and 4 kids). The kids enjoyed sharing the bunk room together and were...
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    About this property
    Tucked away in the woods near Londonderry, Sherwood Escape offers visitors peace, quiet, and the comforts of home for up to eight guests (four adults). The warm wood interior complements the home's secluded setting, so make yourself comfortable in this spacious cabin! Bromley Ski Resort's slopes...
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    Londonderry, Vermont 05148
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wardsboro
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home has a long, country driveway that offers seclusion and privacy. You are greeted by beautiful mature maple trees, a pastoral setting, and a vintage craftsman-style home. The land is 140 acres of woods and open meadows; also featuring large raised bed vegetable gardens, a babbling brook, an...
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    Wardsboro, Vermont 05355
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bondville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Patio
    • Washer
    • Grill
    • Housekeeping Included
    • Terrace
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Convenience is key with this prime location, offering mountain views and free shuttle to the lifts on site. Walk out the door, jump aboard the Strattonwald shuttle, and be on the lift faster than you can post your #OOTD (outfit of the day). APRÉS SKI? This house is both your home and destination...
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    Bondville, Vermont 05340
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charming Vt. Farmhouse with spectacular mt. views. Children welcome1 / 22
    (2)Excellent
    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    • Mountain Views
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Humphreys Farmhouse, a 65-acre year-round vacation home in Vermont. Located in the heart of the Green Mountains minutes away from skiing in the winter, and hiking, swimming and many other activities in the summer, Humphreys Farm is a great place to get away from it all and have fun....
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    Location Information
    Londonderry, Vermont 05148
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stratton 4 Bedroom Home1 / 10
    (9)Very good
    Stratton Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Mountain Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bed Room Mins from the mountain Great Views of the trails 3.7 Miles to Stratton Base 3.0 Miles to Stratton Sunbowl 1.0 Mile to Stratton Golf School 11.5 Miles to Bromley 12 Miles to Magic mountain 16 Miles to Mt. Snow 27 Miles to Okemo Up: MBR King Sleigh w/Pvt Bath AC in MBR, Great Room and...
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    Location Information
    Stratton Mountain, Vermont
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Wardsboro
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 2006, the home underwent it's first extensive renovation by Patrick (Master Builder and Co-Host of DIY's TV Show, Backyard Goldmines). He built the foundation and framed the current home. (Chris and Patrick are siblings) This year, there are new countertops and all the beds are brand new with...
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    Wardsboro, Vermont 05355
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Historic Ski Home - 8 min to Mount Snow1 / 5
    (1)Excellent
    West Wardsboro
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Housekeeping Included
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    We loved our stay at this house! 10 of us came up for the weekend to run the Tough Mudder and we were able to relax in comfort. No wifi and very bad signal kept everyone...
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    About this property
    This gorgeous home is situated in Wardsboro was built in the early 1800's. It was known as 'Levi Sipps Tavern' and served as a Bed & Breakfast and Tavern. In 2013 the home underwent an extensive renovation. It is very close to Mount Snow & Stratton Mountain. Our guests also enjoy golf, shopping,...
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    Location Information
    West Wardsboro, Vermont 05355
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 11
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    Manchester to Stratton - Taking Inquiries for the Summer Horse Show1 / 14
    (1)Excellent
    Bondville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • DVD Player
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2018
    The house is perfectly located close to Manchester and nearby mountains. Kitchen and bedrooms were fully equipped with anything we needed during our trip. king bed in the master...
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    About this property
    This property is snuggled between Stratton Mountain Resort and Manchester center for a perfect alternative to the hustle and bustle of both. The property sits on its own private half-acre and offers mountain views of the Equinox Valley. Guests visiting in the winter have Stratton, Bromley and Magic...
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    Location Information
    Bondville, Vermont 05340
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family Lodge btwn Stratton & Mt. Snow1 / 18
    (6)Excellent
    Stratton Mountain
    5 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Private Garden
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    Really enjoyed my stay here for a snowboarding trip. The house is spacious, super clean, and located very convienently to the mountains. The hosts, Albert and LeAnn, are...
    Reviewed 3 February 2018
    Stayed here for a snowboarding weekend and had the best time! Al and Leann’s were place were super cozy and a good combination of a modernized cabin. The place is spacious and...
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    About this property
    Perfect vacation home situated on a quiet street between Stratton and Mount Snow. 8 minutes to Stratton Sun Bowl Base , 15 minutes to Mount Snow. 30 Min to Manchester for shopping and Fine Dining Minutes to Grout Pond and Stratton Recreation Center to enjoy the great outdoors. 5 bedrooms 2 baths....
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    Location Information
    Stratton Mountain, Vermont 05360
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 11
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    Large, Lovely, Affordable Mountain Home1 / 20
    (3)Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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...
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    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...
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    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stratton Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Internet Access
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 50 yards from some of Stratton's best skiing, this family-friendly and inviting townhome matches mountain views with a high-end atmosphere. Five stories of luxury furnishings, decks, and a private hot tub await your group during a stay here. With a quiet location, this home is especially well...
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    Location Information
    Stratton Mountain, Vermont 05360
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    Stratton Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Stratton Mountain home gives you the best of both worlds: cozy comforts for relaxation and easy access to incredible activities and amazing amenities all year-round! This Long Trail House condo offers access to a shared outdoor heated pool, sauna, and hot tubs, as well as shopping and...
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    Location Information
    Stratton Mountain, Vermont 05356
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stratton Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Sauna
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the exclusive High Meadows section, this gorgeous home offers the very best panoramic view of Stratton Mountain. With a sleek design scheme that blends rustic and modern finishes creating an elegant ambiance, this 4,800 SF luxury home is the beautiful space to return to after a day on...
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    Location Information
    Stratton Mountain, Vermont 05340
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Gorgeous mountain home w/ private hot tub - skiing nearby!1 / 30
    (1)Excellent
    Bondville
    4 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • Mountain Views
    • Washer
    • Grill
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect place to take your next vacation, why not escape to this relaxing Bondville, Vermont getaway? This vacation rental offers a wonderful outdoor patio area with a private hot tub and room for up to eight! Located just five miles from Bondville, this quiet and remote...
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    Bondville, Vermont 05340
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    West Wardsboro
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Shared Indoor Pool
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best of all four seasons in Vermont. This spacious and open concept chalet is on a serene setting on 2.2 acres with pond, and fire pit, mature trees, and perennial gardens. Perfectly located between Mount Snow and Stratton Mountain. Great room has a gorgeous floor to ceiling double sided...
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    Location Information
    West Wardsboro, Vermont 05360
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute Vermont farmhouse is just 10 minutes to Magic, 20 minutes to Bromley and 25 minutes to Stratton. On the main level there is the master bedroom with a full bath, kitchen, dining, and large living area with a comfortable fireplace and a bonus woodstove to keep you extra warm during those...
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Internet Access
    • Balcony
    • Patio
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the Vermont vacation you've always dreamed of at this three-bedroom townhouse, a cozy Stratton retreat with a private balcony, easy access to a shared hot tub and recreation center, and an unbeatable location for skiing and golfing. This light-filled townhouse sits on the east side of...
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    Location Information
    Bondville, Vermont 05360
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Grafton
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a home-away-from-home hidden in the trees when you venture to this 2-bedroom, 1-bathroom vacation rental house that sleeps up to 6 guests in Grafton! Architecturally designed and beautifully unique, this cottage is a picture-perfect scene, secluded from the bustle of the big city so you can...
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wardsboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Internet Access
    • Balcony
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to stay in this spacious yet cozy home in Wardsboro for your next Vermont getaway and enjoy amenities like a game room and large deck in a peaceful wooded setting. And to make your vacation complete, bring the family dog along, too, for a small nightly fee! This home is nestled in the Green...
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    Location Information
    Wardsboro, Vermont 05355
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Windham
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If the mountains of Vermont are calling your name, come stay in this beautiful, modern cabin in the woods and revel in its superb blend of upscale design and quiet, tranquil seclusion. You can bring along your beloved dog, as well, for a small nightly fee! You'll be nestled in tall evergreens,...
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    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Stratton Mountain
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
    • Sauna
    • Internet Access
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright and cheery, this Stratton condo allows you to hit local hot spots and experience a variety of outdoor adventures without hassle! With access to a variety of shared amenities, you'll find that this home has everything you'll need for a fun-filled stay. Located in the Vantage Point...
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    Location Information
    Stratton Mountain, Vermont 05155
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Bondville
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
    • Parking
    • Hot Tub
    • Washer
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Stratton for your upcoming mountain getaway and enjoy a shared pool and hot tub (during summer months), as well as easy mountain access, when you stay in this two-bedroom, family-friendly condo. Walk to the village or catch the nearby shuttle to the mountain, and revel in the simplicity...
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    Location Information
    Bondville, Vermont 05155
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    West Wardsboro
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take your pick of some of Vermont's best slopes at this two-bedroom West Wardsboro home, a dog-friendly retreat with a private deck and firepit, a wood-burning stove, and an ideal location near Mt. Snow and Stratton Mountain Resort! You'll find this home near the center of West Wardsboro, offering...
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    Location Information
    West Wardsboro, Vermont 05360
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Windham
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a Vermont vacation from the pages of a magazine at this three-bedroom Windham home, a secluded country house with an open living space, an expansive deck and yard, and nearby access to picturesque villages, hiking trails, and ski slopes! This home sits on a grassy, tree-lined property...
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    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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