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Pet-friendly vacation rentals in Windham

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windham

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

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Cabin in Londonderry

4.82 out of 5 average rating, 446 reviews

Stunning Rustic Apple Barn - hot tub & sauna

VT’s #1 dream cabin with an overall 5 star rating since 2014 on airbnb! Brand new 4 person private hot tub, sauna & outdoor shower included! Clawfoot tubs inside & out! Originally a horse barn & tack room… We salvaged an old cattle barn for the remodel of this dream home!!! The rustic charm is 100% intentional and every original barn board and nail is back in place! This is upscale cabin living (Wolf and GE appliances) with an original VT antique vibe. Minutes to Magic, Bromley, Stratton, Okemo

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 Londonderry

4.95 out of 5 average rating, 150 reviews

Summit ViewCottage:Cozy 3bd 2ba w/Fireplace&HotTub

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 6 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

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 Jamaica

4.89 out of 5 average rating, 370 reviews

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

Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly (sorry, no cats due to allergies).

Guesthouse in Springfield

4.86 out of 5 average rating, 352 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Cabin in Newfane

4.95 out of 5 average rating, 153 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.

Home in Windham

4.87 out of 5 average rating, 101 reviews

Magic Creek

Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

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”.

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

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

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

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.

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Popular amenities for Windham pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Dummerston

4.99 out of 5 average rating, 338 reviews

Pinecone Pond

Home in Wardsboro

4.95 out of 5 average rating, 100 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Home in Winhall

4.95 out of 5 average rating, 123 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Home in Sunderland

4.97 out of 5 average rating, 236 reviews

MOUNTAIN NEST, views, Manchester, hot tub,

Home in Danby

4.96 out of 5 average rating, 215 reviews

Comfortable farmhouse with stunning views

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Home in Poultney

4.93 out of 5 average rating, 102 reviews

Cozy Home in Poultney, Vermont.

Home in Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Pet-friendly home rentals with a pool

Home in Colrain

4.89 out of 5 average rating, 121 reviews

The 1770 House

Home in Mendon

4.88 out of 5 average rating, 230 reviews

Ranch at Mendon Mt Orchards

Home in Killington

4.98 out of 5 average rating, 120 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

Cabin in Wardsboro

4.93 out of 5 average rating, 192 reviews

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

Guesthouse in Granville

4.9 out of 5 average rating, 854 reviews

Moon Valley Country Retreat no clean fee pets yes

Home in Keene

4.93 out of 5 average rating, 205 reviews

The Brick House on Washington Street

Condo in Killington

4.94 out of 5 average rating, 233 reviews

Dog-Friendly 2BD/2BA Oasis - Pool, Hot Tub & Spa

Rental unit in Clarendon

4.92 out of 5 average rating, 146 reviews

Vermont Horse Farm

Private, pet-friendly home rentals

Cabin in Putney

4.98 out of 5 average rating, 390 reviews

Vermont Retreat Cottage |Exquisite Romantic Escape

Cabin in Granville

4.98 out of 5 average rating, 159 reviews

Quaint log cabin nestled in the woods

Tiny home in Orange

4.92 out of 5 average rating, 346 reviews

The Writer's Retreat: A Sweetwater Stay

Chalet in Dover

4.92 out of 5 average rating, 288 reviews

A charming VT chalet

Cottage in Dorset

4.96 out of 5 average rating, 140 reviews

Pond Cottage

Rental unit in Newfane

4.97 out of 5 average rating, 433 reviews

Rock River Retreat: VT Oasis Pet Friendly

Cabin in Winhall

4.9 out of 5 average rating, 164 reviews

Contemporary 4 bdrm Cabin Hot Tub and Sauna

Guesthouse in Londonderry

4.93 out of 5 average rating, 188 reviews

Beautiful Guest House near Bromley, Magic, Okemo

Quick stats about vacation rentals that are pet-friendly in Windham

Total rentals
20 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
530 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore