
Pet-friendly vacation rentals in Windham County
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Top-rated pet-friendly home rentals in Windham County
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Snug Chalet - Wi-Fi + Close to Mount Snow
This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).
PetsOutdoor spacesCondition

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.
WalkabilityOutdoor spacesRiver

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants
Outdoor spacesPetsAccuracy

The Woodland A-Frame
Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats
Outdoor spacesPetsSleep quality

Luxury “Tiny” House With Sauna (Timbery)
The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.
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Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.
Outdoor spacesWalkabilityPool

Rustic Cabin in foothills of Green Mountains
Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.
PetsOutdoor spacesCheck-in

Beautiful rustic woods and fields retreat.
Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog
WalkabilityOutdoor spacesSkiing

Classic Vermont A-Frame | Fire Pit | Near Stratton
Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.
PetsOutdoor spacesSkiing

Cozy Cabin in Southern VT
Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed.
WalkabilityOutdoor spacesFamily

Cabin getaway in Southern Vermont
Let us share our little piece of Vermont with you! Located off a dirt road, tucked into a corner of our working homestead, you'll find a space to relax, unwind, and reconnect. This cabin has everything you need for a private and comfortable escape. Downstairs you’ll find a comfortable leather couch, small kitchen, & bathroom with vanity & shower. The bedroom (located upstairs) has a queen sized bed. All linens provided.
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Mt Snow Chalet: Peaceful Escape w/Hot Tub
Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰
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Popular amenities for Windham County pet-friendly home rentals
Pet-friendly house rentals

Clark Farm-2 Master-Suites, Great kitchen, views!
WalkabilityOutdoor spacesWifi

Spacious Brattleboro home on river, walk to town
WalkabilityOutdoor spacesView

Pinecone Pond 30 min ski Mt Snow, 45 to Stratton
Outdoor spacesWalkabilityLaundry

Shred Shack: A/C | Hot Tub | Sauna | EV charger
Outdoor spacesWalkabilityView

Modern 3-bedroom A-frame in Londonderry w/ Pond
Outdoor spacesWalkabilityAccess

Peaceful Beautiful Mountain Home Spectacular Views
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The Grafton Chateau
Outdoor spacesWalkabilityGrill

Modern Spacious Home with Mountain Views
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Pet-friendly home rentals with a pool

Log Cabin Near Stratton/Mt Snow
Outdoor spacesWalkabilityView

Rustic Sunny Vermont Home near Mount Snow
PetsWalkabilityParking

Leonard’s Log - Private Hot Tub, Fire Pit, A/C
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“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace
PetsOutdoor spacesBathroom

Woodsy Retreat Near Skiing, Private Pool in Summer
Outdoor spacesWalkabilitySleep quality

Skybarn Vermont: Pool, 100-Mile Views, Historic
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Chalet | Heated Pool + Hot Tub | near Stratton, VT
Outdoor spacesPetsLong stay

The Vermont Barn (Mount Snow)
PetsWalkabilityKitchen
Private, pet-friendly home rentals

The King's Cottage
WalkabilityOutdoor spacesHeating

~Serene Barn Retreat~
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Shakespeare’s Folly Side Farm and AirBnB.
Outdoor spacesWalkabilityWifi

**Happy Hour! Gorgeous & Modern Downtown Retreat**
WalkabilityPetsKitchen

Pet Friendly Silk Purse Cottage on Baker Brook
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Peaceful Forest Studio
WalkabilityOutdoor spacesSkiing

Designer Chalet w/ Mountain Views close to it all
WalkabilityOutdoor spacesHiking

Brook Haven Retreat - Minutes to Mt Snow&Stratton
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Destinations to explore
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- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- June Farms
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Mount Greylock
- Hancock Shaker Village
- Camp Plymouth State Park
- Things to do Windham County
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- Nature and outdoors Vermont
- Food and drink Vermont
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