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Pet-friendly vacation rentals in Windham County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windham County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Cabin in Wardsboro

4.86 out of 5 average rating, 100 reviews

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.

Home in Putney

4.88 out of 5 average rating, 170 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Cabin in Newfane

4.95 out of 5 average rating, 151 reviews

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. We can usually provide a travel crib if requested in advance.

Rental unit in Dummerston

4.96 out of 5 average rating, 195 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Tiny home in Dover

4.99 out of 5 average rating, 167 reviews

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+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Cabin in Putney

4.98 out of 5 average rating, 389 reviews

Vermont Retreat Cottage |Exquisite Romantic Escape

A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Cabins of the East Coast ☽ Elevated, considered design; thoughtful lighting; deeply romantic ☽ A beautiful, Vermont-y drive to Stratton, Okemo, Mt. Snow, Magic & Bromley ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

Chalet in Jamaica

4.98 out of 5 average rating, 241 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, screened-in porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hike, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Barn in Marlboro

4.95 out of 5 average rating, 293 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Cottage in Newfane

4.99 out of 5 average rating, 206 reviews

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”.

Barn in Newfane

4.97 out of 5 average rating, 145 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. 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 $80 per trip per dog

Rental unit in Newfane

4.97 out of 5 average rating, 432 reviews

Rock River Retreat: VT Oasis Pet Friendly

Your private treetop guest suite and beach await at our 1790's colonial on the Rock River in the quiet village of South Newfane, VT. PLEASE READ THE ENTIRE DESCRIPTION BELOW RE: PET POLICIES & kitchenette details. We welcome your furry family members for a $10 fee per pet, per day.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Windham County pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Brattleboro

4.95 out of 5 average rating, 116 reviews

Spacious Brattleboro home on river, walk to town

Home in Londonderry

4.98 out of 5 average rating, 114 reviews

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

Home in Windham

4.87 out of 5 average rating, 101 reviews

Magic Creek

Home in Grafton

4.97 out of 5 average rating, 145 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Home in Putney

4.89 out of 5 average rating, 101 reviews

Peaceful Beautiful Mountain Home Spectacular Views

Home in Londonderry

4.97 out of 5 average rating, 130 reviews

Wild Blossom Farmhouse - a lovely family getaway

Home in Grafton

4.94 out of 5 average rating, 108 reviews

The Grafton Chateau

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Pet-friendly home rentals with a pool

Cabin in Wardsboro

5 out of 5 average rating, 61 reviews

VT Cabin | AC | Firepit | Hike | Swim | Ski

Chalet in Wilmington

4.85 out of 5 average rating, 59 reviews

Cabin | Chalet | Mt Snow | Hot Tub & Pool Access

Chalet in Wilmington

5 out of 5 average rating, 20 reviews

A Chalet 4 All Seasons

Cabin in Wardsboro

4.93 out of 5 average rating, 191 reviews

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Cabin in Wilmington

4.93 out of 5 average rating, 45 reviews

Bear Tracks Cabin - VT Escape

Home in Wilmington

4.77 out of 5 average rating, 52 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!

Cabin in Wilmington

5 out of 5 average rating, 28 reviews

Trending Family Fall Cabin HotTub, Pool, Arcade

Chalet in Wilmington

5 out of 5 average rating, 78 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Private, pet-friendly home rentals

Cabin in Landgrove

4.99 out of 5 average rating, 170 reviews

The Owl’s Nest in Landgrove

Cabin in Brattleboro

4.88 out of 5 average rating, 484 reviews

Cottage

Rental unit in Town of Rockingham

4.82 out of 5 average rating, 171 reviews

Apartment on Main Street

Cabin in Jamaica

4.89 out of 5 average rating, 370 reviews

Forest Cabin-Swim-Views-Fire Pit-7 min to Stratton

Rental unit in Putney

5 out of 5 average rating, 102 reviews

Peaceful Forest Studio

Tiny home in Jamaica

4.94 out of 5 average rating, 1,211 reviews

Apple Blossom Cottage: A Tiny House

Chalet in Dover

4.86 out of 5 average rating, 232 reviews

The Mountain A-Frame at Mount Snow

Cabin in Stratton

4.99 out of 5 average rating, 160 reviews

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

Destinations to explore