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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

Guest favourite
Home in Chester
4.98 out of 5 average rating, 210 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

SarahRating, 5 stars3 weeks ago
This is our second visit in the Recycle House. It’s such a lovely oasis. We love all the unique touches and creative uses of materials throughout the house. The location just steps from the charming town of Chester could not be better. The perfect CT weekend getaway!
Guest favourite
Home in Feeding Hills
4.89 out of 5 average rating, 977 reviews

Farm Fresh Feeding Hills

KaitlynRating, 5 stars3 days ago
A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.
Superhost
Home in Woodstock
4.86 out of 5 average rating, 28 reviews

3-bedroom cottage in serene Lake Bunggee area

LexieRating, 5 stars1 month ago
We had the most wonderful stay in Woodstock while vending at the Brimfield flea market. It was so nice to have a peaceful getaway during the show to sleep well at night. The kitchen was fully stocked with all essential cookware and even seasonings/sauces to assist our meals. Same with the bathroom! The house was cozy and clean, clear and easy instructions in the manual. Mike messaged frequently to check on us and was very kind. Can’t wait to come back to this little woodsy oasis!
Superhost
Home in Ellington
4.8 out of 5 average rating, 66 reviews

Cheerful 3 bedroom home with large back yard

Olga MariaRating, 5 stars5 days ago
Mr. Andrew was great! Made sure we didn't go without. On my next trip I would LOVE to come back. I felt right at home.
Superhost
Home in Ashford
4.85 out of 5 average rating, 94 reviews

Amazing lake home w/ amenities.

StevenRating, 5 stars1 month ago
Needed a last minute place to stay for a few days, Jason’s place worked wonderfully for what we needed. Fast and responsive communications helped lots for us. Overall, very positive experience.
Guest favourite
Home in Mansfield
4.79 out of 5 average rating, 48 reviews

Stunning Mansfield Getaway near UConn & ECSU

BethRating, 5 stars1 week ago
This was a great place to stay for 3 of us using all 3 bedrooms. We found it convenient to get to an event we were attending and easy to get to other towns in the area and back to the airport. The house was comfortable and had everything we needed for a 2-night stay. There were clear instructions and helpful recommendations.
Guest favourite
Home in Montville
4.9 out of 5 average rating, 102 reviews

Spacious-5 Beds! 3 Mi to Mohegan

manrajRating, 5 stars2 weeks ago
They were an amazing host were able to accommodate any last minute changes! The space was great will look forward to the next booking!
Guest favourite
Home in Montville
4.8 out of 5 average rating, 51 reviews

Cozy Cape on the Cove

RebeccaRating, 5 stars2 days ago
We had a wonderful weekend at Deborah’s place. It was perfect for a relaxing weekend close to the casinos and beaches. We enjoyed time fishing on the property, playing cornhole, and roasting marshmallows. Deborah was so kind and hospitable. She left us so many snacks and items for breakfast ❤️ we appreciated it so much. Definitely would recommend staying

Pet-friendly home rentals with a pool

Top guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favourite
Bungalow in Easthampton
4.92 out of 5 average rating, 504 reviews

The Creation Station

KennyRating, 5 stars1 month ago
Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.
Guest favourite
Flat in Burlington
4.86 out of 5 average rating, 111 reviews

Charming apartment with breathtaking view!

AshleyRating, 5 stars2 days ago
Highly recommend Patrick and Monica’s location. You feel right at home when you walk! The pool and patio views are breathtaking. The beds are very comfortable. Patrick was super responsive to my messages regarding restaurants.
Top guest favourite
Home in Stonington
4.97 out of 5 average rating, 227 reviews

Perfect New England Getaway has a pool/ hot tub

ApoorvRating, 5 stars2 days ago
Went with family for a weekend trip. Tracy and Patrick’s home is lovely, very beautiful and well maintained. And everyone enjoyed including my kid who found a lot of toys to play.
Guest favourite
Flat in Holyoke
4.78 out of 5 average rating, 223 reviews

NE Historical Mansion-pets and pet lovers welcome

SusanRating, 5 stars6 days ago
It's not a private space with a door that locks behind you, but it felt pretty private up on the top floor of that huge old house. The main room is enormous, with plenty of open space if you wanted to do yoga or whatever. The bedrooms are also a good size, and there was lots of space for my dog. It took a moment to get use to not having a sink in the "kitchen" area, but the bathroom sink is kitchen sink sized, and had everything you'd need to clean up breakfast dishes. All in all it was a good value for a place that was virtually private and had 2 bedrooms, AND allowed me to bring my dog.
Guest favourite
Cabin in Glocester
4.93 out of 5 average rating, 91 reviews

Get comfy in the country!

DeborahRating, 5 stars3 days ago
Fabulous property, lots of peace and quiet in a pastoral setting. Being able to interact with the horses and cows was the highlight of our stay! The pool was clean and so nice and refreshing, perfect for taking a dip after a day of sightseeing in the area. Lots of coffee shops and ice cream shops nearby, something for everyone in the family! The host was very communicative and helpful. A 10/10 experience and we definitely would return!
Guest favourite
Flat in Glastonbury
4.89 out of 5 average rating, 438 reviews

Quiet 2 bed room apt w/ private entrance.

JoshRating, 5 stars1 month ago
Alice’s place was great! We’ll be back again for sure.
Guest favourite
Home in Montville
4.95 out of 5 average rating, 151 reviews

Casino Stay & Play House

NurisRating, 5 stars2 weeks ago
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Private, pet-friendly home rentals

Top guest favourite
Tiny home in East Lyme
5 out of 5 average rating, 134 reviews

Luxury Tiny Home Near Rocky Neck

HannahRating, 5 stars3 weeks ago
Beautiful home in a quite peaceful area . Note that it is a little difficult to find if you are traveling at night but John was very helpful in giving directions. Bed was VERY comfortable and house had all the basic amenities you would need from kitchen supplies to personal hygiene items you may have forgotten to bring yourself. Would highly recommend to other guests.
Guest favourite
Flat in Putnam
4.82 out of 5 average rating, 28 reviews

Adult Hideaway Pardise w/Firepit & Loft Bed

BreannaRating, 5 stars1 month ago
This place is perfect for a weekend getaway. You can choose to stay in and enjoy the BnB as is with movies/video games, or go out and explore the abundance of restaurants. Absolutely loved the loft bed and little hideout underneath it! Chrissy had also done a bit of a birthday theme for my best friend (reason we went away), and it was super appreciated!
Top guest favourite
Cottage in Brimfield
4.99 out of 5 average rating, 70 reviews

Cheerful 2 bedroom cottage with lake access.

KathleenRating, 5 stars1 week ago
This was the perfect spot for our mini vacation with our adult son and dog. The house was adorable and comfortable...the beds were especially comfy. The fenced in patio area and sun porch was so relaxing and although no one actually slept on it, the daybed was very comfortable as well. We enjoyed our day trip to Boston and multiple trips to Treehouse Brewery. Gwen's communication was awesome...such a terrific host! Hoping to stay again.
Guest favourite
Farm stay in Coventry
4.93 out of 5 average rating, 314 reviews

Luxury Secluded Home on Equestrian Estate

AbigailRating, 5 stars3 days ago
We had a lovely stay with the horses and spacious rooms! Especially loved the covered outdoor porch so we could enjoy the fresh air even when raining
Top guest favourite
Barn in Hampton
5 out of 5 average rating, 31 reviews

Little Rest Studio

CharlieRating, 5 stars2 days ago
My wife and I had a lovely time staying for the weekend. Walking through the working barn up to the beautiful loft area was a really fun experience. We loved the view from the back deck and the bathroom was really amazing. They have done an amazing job with this place and I highly recommend it to anyone staying in the area!
Top guest favourite
Guest house in Holland
5 out of 5 average rating, 39 reviews

One BD In-law with Private Ent.

TimRating, 5 stars2 days ago
Ryanne’s place was so cute! The neighborhood was quiet and peaceful and the room itself was very private. We wish we could have stayed longer to explore the lake area nearby.
Guest favourite
Tiny home in Scotland
4.9 out of 5 average rating, 21 reviews

Hayfield Hideaway

SamRating, 5 stars1 week ago
The place is a mobile home on a large property. It is well equipped, with nice towels and a nice bed. There was coffee and a dozen eggs (which I imagine were fresh, but I didn't eat them so I can't say for sure -- it was, however, a nice touch!). The place overlooks a lush field, and the day I spent there, it poured like crazy and it was lovely to see and watch the field get soaked. The view was fantastic. My one complaint is that the cleaning fee was $100. That seems too high to me. Based on my experience, a fee of 60-75$ would be more in alignment for a place like this. Other than that, it is a lovely space and well-maintained. P.S. There was very little soap in the bathroom. Fortunately I had a bar soap in my travel pack.
Guest favourite
Cabin in Voluntown
5 out of 5 average rating, 12 reviews

1960s Heirloom Log Cabin on the water

MartinRating, 5 stars3 weeks ago
We had a wonderful stay at this historic cabin in a beautiful location surrounded by trees next to a peaceful lake. Super cozy fireplace in the cabin, BBQ grill and fire pit outside made for a wonderful stay. Would highly recommend!

Destinations to explore