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Windham House Rentals

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    Don't let other travelers get your favorite Windham area vacation rental. You're so close to securing your perfect getaway. Book today.
    25 Matching Rentals in the Windham AreaView all 42 rentals
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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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    The following rentals are within 10 miles of Windham.
    Reilly's Rest in the Green Mountains, Kid and Pet friendly!!1 / 22
    (11)Excellent
    Weston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Yard
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    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...
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    Chester, Vermont 05143
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Sauna
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Bondville, Vermont 05340
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 4
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    Jamaica
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • 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...
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    Jamaica, Vermont 05343
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Peru
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Housekeeping Included
    • Washer
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at Bromley Mountain with mountain trail access from the back door. This newly renovated slope side house is the ultimate in convenience. With two full baths and four bedrooms, it will accommodate an extended family or group comfortably. House also has an updated kitchen and dining area,...
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    Peru, Green Mountains 05152
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Andover
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Private Yard
    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...
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    Andover, Vermont 05143
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Stratton 4 Bedroom Home1 / 10
    (9)Very good
    Bondville
    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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    Bondville, Vermont 05155
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Charming Vt. Farmhouse with spectacular mt. views1 / 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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    Londonderry, Vermont 05148
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    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...
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    Chester, Vermont 05143
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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...
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    Jamaica, Vermont 05343
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Peru
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Door Farm 'Cottage' - Brought to you by Gertrude Rentals! This charming 2BR/2Bath Dutch farm house is just 4mi. to Bromley, 5mi. to Magic, 12mi. to Stratton, and 19mi. to Okemo. It boasts 100% cotton sheets mattresses linens and pillow, and is decorated with antiques and oriental rugs. It...
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    Location Information
    Peru, Green Mountains 05148
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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 Yard
    • 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
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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....
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    Chester, Vermont 05143
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    Rental Home - 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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    Peru
    3 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you're seeking snow-capped mountains or blooming wildflowers, Peru, Vermont has it all! For the ultimate mountain getaway, escape to this 3-bedroom, 2.5-bathroom vacation rental townhouse that comfortably sleeps 11. Recently renovated, this lovely townhome offers pristine appliances,...
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    Peru, Green Mountains 05152
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 11
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    Peru
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Sauna
    • Mountain Views
    • Washer
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on close to 5 secluded acres in Vermont's Green Mountains, the Vermont Mountain House is located in Peru, VT, a short drive from the beautiful town of Manchester and located next to four ski resorts for all levels: Bromley, Stratton, Okemo, and Magic Mountain, as well as Hapgood swimming...
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    Location Information
    Peru, Green Mountains 05152
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Landgrove
    8 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Wi-Fi
    • Grill
    • Patio
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    • Balcony
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private resort is the perfect setting for your luxury corporate retreat, wedding, reunion, or any large gathering. THIS PROPERTY IS 100% NUT FREE! When guests aren't here Henry a toddler with a fatal nut allergy is. Thank you in advance and I really appreciate your understanding. Set on 10...
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    Landgrove, Vermont 05148
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 22
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    Grafton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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...
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    Grafton, Vermont 05146
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
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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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    Grafton, Vermont 05146
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Landgrove
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in the 1830s by the town blacksmith, this property has been in our family for over 80 years. This house has such a good vibe! In the winter months snowboarding, downhill skiing, cross country skiing, snowshoeing and snowmobiling are literally minutes away. In warmer months,...
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    Landgrove, Vermont 05148
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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