Pet-friendly vacation rentals in Windham

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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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Guest favorite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.85 out of 5 average rating, 165 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.

Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 230 reviews

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

Top guest favorite
The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.
Home in Weston
4.95 out of 5 average rating, 303 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Top guest favorite
A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.
Barn in Andover
4.99 out of 5 average rating, 142 reviews

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Guest favorite
A charming treehouse is nestled in a snowy landscape, elevated on stilts with a wraparound deck. Soft white lights illuminate the exterior, while snow gently falls around it. A wooden staircase leads up to the entrance, highlighting the inviting ambiance.
Treehouse in Londonderry
4.88 out of 5 average rating, 149 reviews

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Guest favorite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Apartment in Dummerston
4.95 out of 5 average rating, 253 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.

Superhost
Home in Jamaica
4.86 out of 5 average rating, 304 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Guest favorite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,316 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Superhost
The timber frame house is surrounded by dense trees, showcasing a natural setting. Large windows illuminate the exterior, providing glimpses of the interior. Sturdy wooden steps lead to the door, enhancing accessibility amid the forest environment.
Tiny home in Athens
4.92 out of 5 average rating, 233 reviews

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.

Top guest favorite
A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.
Cottage in Jamaica
4.84 out of 5 average rating, 591 reviews

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

Guest favorite
Cabin in Winhall
4.96 out of 5 average rating, 369 reviews

Dog Friendly A-Frame Retreat near Hiking, Skiing

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Top guest favorite
A charming red cabin is positioned amidst lush greenery, with a wraparound deck accessible from the front. Bright yellow flowers bloom in abundance in the foreground, enhancing the natural beauty of the serene setting.
Cabin in Newfane
4.95 out of 5 average rating, 209 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.

Popular amenities for Windham pet-friendly home rentals

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

  • Total vacation rentals

    Explore 20 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at € 110 per night before taxes and fees

  • Verified guest reviews

    Over 870 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Windham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windham rentals

  • 4.9 Average rating

    Windham stays are highly rated by guests—averaging 4.9 out of 5!

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