
Pet-friendly holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County pet-friendly home rentals
Pet-friendly house rentals

Spacious Brattleboro home on river, walk to town
It was perfect for my overflow guests attending a weekend family reunion!

The Sugar House
The Sugar House was a fantastic place to stay! It was quiet and peaceful and there was a ton to explore in Burlington VT. The house had a lot of charm. it was cozy, warm, and had everything we needed for the weekend!

Pinecone Pond
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.

Frosted Willows
We had a lovely stay, while in town celebrating our friend’s marriage! We really enjoyed the creek in the backyard! We would recommend this wonderful home ☺️

1850's VT Farmhouse on the River
We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We stayed for a weekend at Kelley and Jason’s home in Vermont and everything went great. From check in, to the local recommendations, to the quiet setting, we enjoyed a great time away. Hot tub, game room and the large deck were great.

The Grafton Chateau
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.

Wild Blossom Farmhouse - a lovely family getaway
We had a wonderful weekend in Vermont! The Airbnb was beautiful, clean and in a great location!
Pet-friendly home rentals with a pool

Cabin | Chalet | Mt Snow | Hot Tub & Pool Access
The stay was exactly as described in the photos and listing. Brian provided everything I needed for a productive working vacation—high-speed internet, comfortable accommodations, and a peaceful environment to relax and recharge during downtime. Highly recommend!

Leonard’s Log - Private Hot Tub, Fire Pit, A/C
The cabin was lovely! We went for a little weekend getaway with some friends and it is a great space for such an occasion. There is a surprising amount of space in and around the house and we didn't even use the three season porch. The hosts were also very responsive and easy to communicate with. Definitely a cute little home away from home!

Family/Dog Friendly Mountain Home w/ Amenities
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
We loved the Snow Chalet!! Such beautiful surroundings and well appointed. The beds were super comfy and the black out shades were great for the kids. Location was great and close to the grocery stories. Wilmington is a sweet town too with lots of cool shops. The club house pool was warm and the pool was nice and toasty. An awesome trip!

Wander In | Close to Mount Snow & Stratton
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Lovely house can’t wait to rebook for next snowboard trip!

The Vermont Barn (Mount Snow)
My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!
Private, pet-friendly home rentals

#32 Top Floor-Newly Renovated! Room 32-Horizon Inn
Great stay, location was just right, very clean and comfy with some additional touches for a nice weekend getaway!

Cottage
A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.

Apartment on Main Street
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

Snug Chalet - Wi-Fi + Close to Mount Snow
We loved our time in West Dover! The house is perfectly situated between West Dover and Wilmington! Our dogs loved the fenced in area and we loved the deck, the open concept space and the proximity to town. We will definitely be back!

The Carriage Barn
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike
Lovely cabin, with great hiking opportunities nearby. Brandon is super responsive and helpful. Had a great time, even if one day it rained all day!

Vermont Retreat Yurt-Outdoor Bathtub in Nature
This was a beautiful, relaxing, and perfectly located spot! The yurt was spacious, clean, and well set up with a small living area, two cushy chairs and comfortable bed. The lighting situation inside was lovely with soft lights everywhere to find your ideal set up! The front porch had its own natural light show with fireflies at dusk. There is a wooden walk bridge to the shower and the composting toilet. Overall- simply lovely and incredibly relaxing.

Rock River Retreat: VT Oasis Pet Friendly
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Destinations to explore
- Bed and breakfasts Windham County
- House rentals Windham County
- Rentals with pools Windham County
- Rentals with beach access Windham County
- Rentals with outdoor seating Windham County
- Rentals with an accessible height toilet Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with breakfast Windham County
- Rentals with a sauna Windham County
- Rentals with a fire pit Windham County
- Rentals with lake access Windham County
- Private suite rentals Windham County
- Rentals with a patio Windham County
- Rentals with a fireplace Windham County
- Chalet rentals Windham County
- Rentals with a hot tub Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Rentals with a kayak Windham County
- Beachfront rentals Windham County
- Rentals with an EV charger Windham County
- Cabin rentals Windham County
- Family-friendly rentals Windham County
- Condo rentals Windham County
- Fitness-friendly rentals Windham County
- Farmstay rentals Windham County
- Rentals with a washing machine and dryer Windham County
- Townhouse rentals Windham County
- Tiny house rentals Windham County
- Apartment rentals Windham County
- Pet-friendly rentals Vermont
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club
- Bretwood Golf Course