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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, 103 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.

Cabin in Jamaica

4.87 out of 5 average rating, 291 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

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, 168 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.

Barn in Marlboro

4.95 out of 5 average rating, 294 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, 207 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 Town of Rockingham

4.95 out of 5 average rating, 253 reviews

Stunning Studio in historic Downtown Bellows Falls

Beautifully curated and spacious studio located in historic downtown Bellows Falls, VT. Come to escape the hustle and bustle of a big city without giving up metropolitan amenities. With a great location, you can walk to the train station, local bars and restaurants, shops, movie theater, etc. From the studio, you are a short distance drive to many outdoor activities that Vermont has to offer such as hiking, kayaking, mountain biking, etc.

Cabin in Putney

4.9 out of 5 average rating, 130 reviews

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.

Loft in Wilmington

4.93 out of 5 average rating, 187 reviews

Walk to Village/Lake Whitingham

The garage apartment is comfortable, clean and pet-friendly. Great for weekend getaways; we are just a stroll away from the lake or the village and a short drive to Mount Snow. The Moover is a local free bus to Mount Snow ski resort, Brattleboro and Bennington and is easily accessible at the traffic light.

Rental unit in Newfane

4.97 out of 5 average rating, 433 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

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

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 Brattleboro

4.95 out of 5 average rating, 169 reviews

Frosted Willows

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

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

Home in Wilmington

4.99 out of 5 average rating, 188 reviews

Vermont Sugar House Retreat

Home in Grafton

4.97 out of 5 average rating, 146 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 Grafton

4.94 out of 5 average rating, 108 reviews

The Grafton Chateau

Home in Wardsboro

4.94 out of 5 average rating, 148 reviews

Sawmill Road - between Stratton and Mount Snow

Pet-friendly home rentals with a pool

Townhouse in Dover

4.98 out of 5 average rating, 51 reviews

Enjoy a whimsical escape only minutes from Mt Snow

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

Cabin in Wardsboro

4.93 out of 5 average rating, 192 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

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, 79 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Farm stay in Grafton

4.84 out of 5 average rating, 25 reviews

Jack Taylor Farm (with Alpacas!)

Private, pet-friendly home rentals

Cabin in Landgrove

4.99 out of 5 average rating, 171 reviews

The Owl’s Nest in Landgrove

Cabin in Jamaica

4.89 out of 5 average rating, 370 reviews

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

Tiny home in Jamaica

4.94 out of 5 average rating, 1,213 reviews

Apple Blossom Cottage: A Tiny House

Chalet in Dover

4.94 out of 5 average rating, 117 reviews

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

Chalet in Dover

4.86 out of 5 average rating, 233 reviews

The Mountain A-Frame at Mount Snow

Rental unit in Brattleboro

4.8 out of 5 average rating, 90 reviews

Artsy Studio w/Fireplace - Pet-Friendly!

Guesthouse in Chesterfield

4.99 out of 5 average rating, 69 reviews

House on a hill

Cabin in Wilmington

4.93 out of 5 average rating, 441 reviews

Picturesque Cabin near Mt Snow

Destinations to explore