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Vacation Rentals in Windham, VT and nearby

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    1 / 20
    4.5 of 5 stars (3) Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    The following rentals are within 15 kilometres of Windham, Vermont.

    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    1 / 10
    4 of 5 stars (1) Very good
    Chester
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 11
    5 of 5 stars (10) Excellent
    Weston
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    • Mountain Views
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Description of the house: • 1600 square foot, all cedar, spacious two-story house. • Situated on over 6 very private acres. • Features an open layout with a large deck and a large wood-burning fireplace. • Has 3 private bedrooms (13x13, 11x13, and 10x10) and 2 full bathrooms (one up one down). •... View all property information
    Location Information
    Weston, Vermont 07601
    4 of 5 stars Reviewed 19 February 2016
    Very nice Cabin. Great location between many ski mountains and hiking trails. Excellent fireplace and living room/dining room area. Plenty of space for multiple guests with 3...
    5 of 5 stars Reviewed 14 December 2015
    We were so happy with the rental house, all the instructions were very clear and the weather was just perfect. It is a charming rustic home in the woods of Vermont. Each bedroom...
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    Chester
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    • Washer
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    • Mountain Views
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    • Pet-friendly
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    • x
    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
    1 / 22
    5 of 5 stars (2) Excellent
    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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.... View all property information
    Location Information
    Londonderry, Vermont 05148
    1 / 12
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Central Heating
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    About this property
    Grafton Log Home: Charming log house in an Alpine-like meadow with great views in a peaceful setting. This home is equipped with a fireplace, eat in kitchen, dining area, 4 bedrooms (sleeps 8), 2 baths, and large deck. Internet Located about 4 miles from center of town, on a dead-end gravel... View all property information
    Location Information
    Grafton, Vermont 05146
    1 / 10
    Bondville
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Satellite TV
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    4 BR Mins from the mountain Up: MBR King Sleigh w/Pvt Bath AC in MBR Down: BR w/Queen, BR w/Queen, BR w/2 bunks, pull out couch - Double/Queen No Shuttle Bus Some dates are negotiable - make offer Beds: 1 King Bed, 2 Queen Beds, 4 Twin Beds, 1 Sofa Bed, 1 Crib View all property information
    Location Information
    Bondville, Vermont 05155
    Peru
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Rustic Log Home located on 10 secluded acres in quintessential Peru. Our property is very private and is our primary home 9 months out of the year. Please care for our home as if it were your own. This home is a summer rental only. Although our home is 3 bedrooms, we can sleep up to 10 people.... View all property information
    Location Information
    Peru, Green Mountains 05152
    Peru
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Porch
    • Mountain Views
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ski to and from this slopeside getaway located at one of Vermont' finest ski Resorts. View all property information
    Location Information
    Peru, Green Mountains 05152
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    1 / 23
    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Waterfront
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    • ?
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    • x
    About this property
    Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of... View all property information
    Location Information
    Chester, Vermont 05143
    1 / 13
    5 of 5 stars (1) Excellent
    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • ?
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    • x
    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
    5 of 5 stars 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 we...
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    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    House is super clean with new roof, newer carpet & newer interior paint!! Open floor plan with wood burning stove. Very clean & comfortable. Perfect for families or group of friends. Open floor plan living room, dining room & kitchen. 1 loft bedroom has king size bed w/ private bath, 1 bedroom... View all property information
    Location Information
    Londonderry, Vermont 05148
    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
    • Internet Access
    • Patio
    • Satellite TV
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    • Washer
    • DVD Player
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Completely remodeled in 2013, this end unit is one of Piper Ridge's most private on a dead end road with only one other neighbor. The townhouse features two king beds in the master and junior suite each with their own bathrooms. The upstairs rooms has two twins and an adjoining "loft" area with a... View all property information
    Location Information
    Bondville, Vermont 05340
    1 / 21
    Peru
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Located on a totally private 10 acre wooded lot in Peru, Vermont. The house was recently repainted. It is close to the best skiing, shopping, dining, swimming, golf & tennis Vermont has to offer. Living area is 32 ft x 48 ft. Fireplace. Cathedral ceiling. 2 sets of French doors open onto a large... View all property information
    Location Information
    Peru, Green Mountains
    Chester
    Private Room, 7 Bathrooms, Sleeps 18 | Quick View
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    • Satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    • DVD Player
    • Porch
    • Internet Access
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    Peru
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Mountain Views
    • Balcony
    • DVD Player
    • Grill
    • Terrace
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Recently renovated townhome on Bromley Mountain. 3 bedrooms plus loft, 2.5 bathrooms. Sleeps 9-11 comfortably. This home is located slopeside, adjacent to one of the trails on Bromley Mountain. In winter, it is less than 100 yards to the top of the Lord’s Prayer lift and you can ski down to the... View all property information
    Location Information
    Peru, Green Mountains 05152
    1 / 24
    Andover
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Patio
    • Hot Tub
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Ski Okemo is 10 minutes away. Snowmobile from this new Townhouse on VAST Vermont Snowmobile Trails, hundreds of miles of marked and groomed trails. Snowmobile rentals available. Free shuttle bus to Ski Mountain across the street. Nearby XC Skiing trail, ice skating area, sledding hill, lakes with... View all property information
    Location Information
    Andover, Vermont
    1 / 7
    Peru
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Location is everything, and this well maintained townhome offers the best, situated in a quiet residential area, yet only a couple of blocks from downtown Manchester amenities. Property is tastefully furnished and spacious, with 3 full levels, and can comfortably sleep 6-8. Additional features... View all property information
    Location Information
    Peru, Green Mountains
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    Grafton
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Grill
    • DVD Player
    • Shared Garden
    • Mountain Views
    • Internet Access
    • Waterfront
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy a getaway situated on the brook, less than a mile from the town center of Grafton. The cabin offers a perfect place for anyone looking for a relaxing and peaceful get-away. We have designed the cabin with the goal of making it a very special place. The cabin was built in 2009 with logs from... View all property information
    Location Information
    Grafton, Vermont 05146
    Jamaica
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • DVD Player
    • Porch
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    • Washer
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    • Satellite TV
    • Mountain Views
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Historic and Serene. Sleeps a Family + Friends, Furry or Otherwise. 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 village, yet quiet and serene. The peaceful sound of water over stones... View all property information
    Location Information
    Jamaica, Vermont 05343
    South Londonderry
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    WINTER SEASONAL RENTAL! This So. Londonderry home is tucked away in a wooded setting but just a quick walk to Solo and just minutes from Stratton, Magic Mountain and Bromley! A well maintained home offering 2,900 sq ft with 4 bedrooms 2 of them master bedrooms, 5 full baths, wood burning... View all property information
    Location Information
    South Londonderry, Vermont 05155
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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
    1 / 25
    Peru
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    This cozy Bromley retreat has great mountain views, is walking distance to ski lifts, and has plenty of space for up to 10 guests to spread out and relax. This duplex rental is in a fantastic location where guests can easily frequent the slopes for downhill skiing and snowboarding, and walk to... View all property information
    Location Information
    Peru, Green Mountains 05152
    1 / 29
    Weston
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
    • Grill
    • Balcony
    • Internet Access
    • Washer
    • Patio
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Four bedroom, two full bath, historic 1820's Saltbox Colonial loaded with character and charm. Very clean and well maintained. Top Floor: MBR: Large, bright and inviting king bedroom connects to full bathroom with his/hers sinks, sliders to private balcony overlooking backyard with beautiful... View all property information
    Location Information
    Weston, Vermont 05161
    Chester
    Private Room, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • Terrace
    • DVD Player
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    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 31
    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • x
    About this property
    With nearby attractions like pristine slopes, picturesque hikes, and relaxing rounds of golf, this Stratton retreat offers the perfect escape from your daily grind! This home is located only a short drive or shuttle ride away from the skiing, hiking, and golfing of the Stratton Mountain Resort and... View all property information
    Location Information
    Bondville, Vermont 05340
    Chester
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    • Porch
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    • Balcony
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    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 26
    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    With easy access to the slopes and all of the comforts of home, this elegant Vermont rental is the perfect choice for a mountain getaway! Located in the Piper Ridge community, this home includes access to a number of amenities, including a clubhouse, indoor swimming pool, hot tub, racquetball... View all property information
    Location Information
    Bondville, Vermont 05340
    Andover
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    LOG HOME 8 MILES FROM OKEMO MOUNTAIN. LOCATED ON TOP OF TERRIBLE MOUNTAIN WITH BEAUTIFUL VIEWS OF MAGIC MOUNTAIN. FULLY EQUIPPED KITCHEN, COFFEE MAKER , MICROWAVE, STOVE, REFRIGERATOR. BEDS ALL HAVE LINENS. THIS IS A TURN KEY. SLEEPS 10 IN BEDS. BEAUTIFUL AND READY TO RENT. HOLIDAY RENTALS... View all property information
    Location Information
    Andover, Vermont 05143
    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
    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
    1 / 30
    Bondville
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    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 10! Located just five miles from Bondville, this quiet and remote... View all property information
    Location Information
    Bondville, Vermont 05340
    Jamaica
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
    • Parking
    • Private Garden
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    This property has now been rented for the 2015-16 season and is no longer available. property has now been rented for the 2015-16 season and is no longer available. property has now been rented for the 2015-16 season and is no longer available. property has now been rented for the 2015-16 season... View all property information
    Location Information
    Jamaica, Vermont 05343
    Grafton
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Built circa 1840, our home, called the West Corner, is nestled in the west end of the village center, providing unusual privacy for an in village home. It is very private, yet only a minute's walk to the main street, village park & the tavern, the general store and churches. Grafton is a very... View all property information
    Location Information
    Grafton, Vermont 05145
    Grafton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The vintage barn studio offers an open living plan with Queen bed, fully equipped gourmet kitchen and a cozy seating area w/ fireplace. Once an artist's studio, it is has been painstakingly renovated with a "reduce reuse recycle" philosophy. The studio it is adorned with beautiful antique wide... View all property information
    Location Information
    Grafton, Vermont 05145
    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    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
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Grafton, Vermont 05146
    1 / 29
    Bondville
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Consider the possibilities when you rent this spacious Vermont retreat, with its own private sauna and easy access to ski and golf. Suitable for your own large group or reunions with family or friends, this vacation home is sure to fulfill your needs. Located in secluded Winhall, this lovely... View all property information
    Location Information
    Bondville, Vermont 05340
    1 / 17
    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Grill
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Classic colonial; Large white 2-story 1819 farmhouse w 5 BR, 3 B, rustic family room w/ fireplace; 2 parlors w fireplace, large eat-in kitchen, DR office w INternet WiFi; cable; phone; BR w fireplace; huge red barn w deck and hottub; lovely small river in back; beautifully furnished w period... View all property information
    Location Information
    Chester, Vermont
    1 / 8
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Parking
    • Central Heating
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful country cottage set on an idyllic 4 acre property, with a majestic view of the mountains, and across the street from the Tater Hill Golf course. In addition to the main house, there is a barn that can accommodate two cars and parking space for at least four additional cars. The... View all property information
    Location Information
    Chester, Vermont 05143