Pet-friendly holiday rentals in Windham County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windham County pet-friendly home rentals

Pet-friendly house rentals

Top Guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 123 reviews

Spacious Brattleboro home on river, walk to town

ThomasRating, 5 stars1 month ago
It was perfect for my overflow guests attending a weekend family reunion!
Superhost
Home in Dummerston
4.96 out of 5 average rating, 130 reviews

The Sugar House

NadiaRating, 5 stars3 months ago
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!
Top Guest favourite
Home in Dummerston
4.99 out of 5 average rating, 347 reviews

Pinecone Pond

KathyRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Brattleboro
4.93 out of 5 average rating, 212 reviews

Frosted Willows

TyRating, 5 stars5 days ago
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 ☺️
Guest favourite
Home in Jamaica
4.81 out of 5 average rating, 405 reviews

1850's VT Farmhouse on the River

MichaelRating, 5 stars8 months ago
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.
Top Guest favourite
Home in Wardsboro
4.95 out of 5 average rating, 111 reviews

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

MikeRating, 5 stars1 month ago
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.
Guest favourite
Home in Grafton
4.94 out of 5 average rating, 120 reviews

The Grafton Chateau

EmmaRating, 5 stars3 months ago
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.
Top Guest favourite
Home in Londonderry
4.97 out of 5 average rating, 142 reviews

Wild Blossom Farmhouse - a lovely family getaway

MorganRating, 5 stars1 week ago
We had a wonderful weekend in Vermont! The Airbnb was beautiful, clean and in a great location!

Pet-friendly home rentals with a pool

Superhost
Chalet in Wilmington
4.86 out of 5 average rating, 77 reviews

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

NickRating, 5 stars2 months ago
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!
Superhost
Cabin in Wardsboro
4.92 out of 5 average rating, 202 reviews

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

AnthonyRating, 5 stars2 months ago
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!
Top Guest favourite
Home in Wilmington
4.96 out of 5 average rating, 28 reviews

Family/Dog Friendly Mountain Home w/ Amenities

LouisRating, 5 stars3 days ago
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.
Top Guest favourite
Chalet in Wilmington
5 out of 5 average rating, 94 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

AmyRating, 5 stars2 months ago
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!
Guest favourite
Home in Wardsboro
5 out of 5 average rating, 8 reviews

Wander In | Close to Mount Snow & Stratton

KatherineRating, 5 stars3 months ago
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.
Guest favourite
Chalet in Winhall
4.88 out of 5 average rating, 106 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

BrandonRating, 5 stars3 months ago
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!
Superhost
Cabin in Wardsboro
4.91 out of 5 average rating, 227 reviews

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow

StevenRating, 5 stars3 months ago
Lovely house can’t wait to rebook for next snowboard trip!
Guest favourite
Home in Wilmington
4.84 out of 5 average rating, 171 reviews

The Vermont Barn (Mount Snow)

AmandaRating, 5 stars3 months ago
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

Guest favourite
Hotel room in Wilmington
4.94 out of 5 average rating, 143 reviews

#32 Top Floor-Newly Renovated! Room 32-Horizon Inn

JuliaRating, 5 stars1 month ago
Great stay, location was just right, very clean and comfy with some additional touches for a nice weekend getaway!
Guest favourite
Cabin in Brattleboro
4.89 out of 5 average rating, 499 reviews

Cottage

LizRating, 5 stars3 days ago
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.
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 186 reviews

Apartment on Main Street

CraigRating, 5 stars1 month ago
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.
Guest favourite
Chalet in Wilmington
4.96 out of 5 average rating, 111 reviews

Snug Chalet - Wi-Fi + Close to Mount Snow

EdwardRating, 5 stars3 weeks ago
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!
Top Guest favourite
Barn in Guilford
4.99 out of 5 average rating, 126 reviews

The Carriage Barn

AristidesRating, 5 stars2 weeks ago
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.
Top Guest favourite
Cabin in Stratton
5 out of 5 average rating, 150 reviews

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

JonathanRating, 5 stars2 weeks ago
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!
Guest favourite
Tiny home in Putney
4.97 out of 5 average rating, 470 reviews

Vermont Retreat Yurt-Outdoor Bathtub in Nature

EmmaRating, 5 stars3 days ago
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.
Top Guest favourite
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars1 week ago
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