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Windham Pet Friendly 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.
    18 Matching Rentals in the Windham AreaView all 46 rentals
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    Modern cabin in the woods - upscale seclusion in tranquil setting, dogs welcome!1 / 31
    (1)Very good
    Windham
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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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.
    Skiing, Farm to Table Foods, Cheeses, Craft Beers - The Blue Door Farm!1 / 48
    (4)Excellent
    Peru
    6 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Peru
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Gertrude Rentals property, The Blue Door Farm 'Cottage' - 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 also...
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    Peru, Green Mountains 05148
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Amenities & Details
    • Parking
    • Mountain Views
    • Washer
    • Grill
    • Central Heating
    • Porch
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 19, 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...
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    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...
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    Location Information
    Jamaica, Vermont 05343
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Landgrove
    8 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Balcony
    • Grill
    • Hot Tub
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Gertrude Rentals property! Enormous farm-house with 6 suites, 8 fireplaces, 5 spa-baths, 8 baths, stained glass windows, commercial cellar bar with stone fireplace, sun-deck, chefs kitchen, sunroom with wall-to-wall windows, hot tub, lush tapestry curtains, Oriental rugs, 100% cotton sheets, and...
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    Landgrove, Vermont 05148
    Rental Home - 8 Bedrooms, 10 Bathrooms, Sleeps 22
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    Weston
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Grill
    • Skiing: Property Is In A Ski Resort
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Idyllic former B&B nestled in rolling Conservancy-Trust-Fields with the West River bank on one side and cows grazing on another. Perfectly located in the shire of Weston. Convenient access to ski mountains Okemo Magic Bromley and Stratton, snowmobiling on the VAST, fly fishing hiking and biking...
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    Weston, Vermont 05161
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    Weston
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Idyllic Vermont cottage nestled in rolling Conservancy-Trust-Fields with the West River bank on one side and cows grazing on another. Perfectly located in the shire of Weston. Convenient access to ski mountains Okemo Magic Bromley and Stratton, snowmobiling on the VAST, fly fishing hiking and...
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    Location Information
    Weston, Vermont 05161
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Trail Side at Bromley Resort Minutes from ManchesterVT, VSF horse show, Stratton1 / 34
    (1)Excellent
    Peru
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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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    Location Information
    Peru, Green Mountains 05152
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Bondville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Bondville, Vermont 05340
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Peru
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Jamaica
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    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...
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    Location Information
    Jamaica, Vermont 05343
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Jamaica
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    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...
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    Jamaica, Vermont 05343
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Bondville
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Bondville, Vermont 05340
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Jamaica
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    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...
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    Location Information
    Jamaica, Vermont 05343
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Andover
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Andover, Vermont 05143
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Jamaica
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    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....
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    Location Information
    Jamaica, Vermont 05343
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    Landgrove
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • 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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    Location Information
    Landgrove, Vermont 05148
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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