Pet-friendly vacation rentals in Roxbury

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Roxbury pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
Home in Millerton
4.96 out of 5 average rating, 191 reviews

Vacation Home In Millerton

SusanRating, 5 stars3 weeks ago
If there were more stars this place would warrant them. Incredibly clean and thoughtfully stocked. The appliances were great, the cupboards were full of dishes, pots and pans. Bed linens were pristine. Very spacious and quiet. We were very happy here.
Guest favorite
Home in West Cornwall
4.91 out of 5 average rating, 188 reviews

Charming CT Country Farmhouse for group getaway

ChrisRating, 5 stars1 month ago
Such a fun old home, reminded my wife of the old farmhouse she grew up in. The location was perfect for our needs and there was enough space for everyone.
Superhost
Home in Cornwall
4.83 out of 5 average rating, 100 reviews

State Forest Getaway

NicoleRating, 5 stars1 month ago
My girlfriends and I had an amazing stay! The house is stunningly gorgeous—even more beautiful than the photos. Every detail was thoughtfully designed, creating the perfect setting for a relaxing and fun getaway. The space was spotless, well-equipped, and incredibly comfortable. We truly had a great time and felt right at home. Highly recommend for anyone looking for a stylish and memorable escape!
Guest favorite
Home in Sharon
4.92 out of 5 average rating, 154 reviews

Nature Cottage w/ Private Path to River Access

EstelleRating, 5 stars2 weeks ago
Place is beautiful and very relaxing. We really enjoyed our stay in the house and the outdoor with the little river was perfect for our young kids
Top guest favorite
Home in Germantown
4.95 out of 5 average rating, 426 reviews

Rustic Swedish Barn/Featured in Airbnb Magazine

GabriellaRating, 5 stars1 week ago
We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!
Guest favorite
Home in Roxbury
4.91 out of 5 average rating, 22 reviews

Serenity in the Roxbury Woods!

KyraRating, 5 stars3 months ago
We enjoyed a wonderful stay! Danny was truly amazing! Very responsive and even checked on us during the winter storm to ensure everything was ok. He also had the snow plow come through and do the driveway prior to checkout. The house is amazing and we can’t recommend Danny’s place enough!
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars1 week ago
Only complaint would be the noise from road during the morning commute
Top guest favorite
Home in Fairfield
5 out of 5 average rating, 108 reviews

Peaceful Suburban Colonial w/New Kitchen.

LizRating, 5 stars1 month ago
Amazing, super clean, immaculate home. From goodies/food/drinks left for us to the squeaky cleanliness of the home we found it worth 10 stars!!! Jon's hospitality as a host was nothing short of amazing!! Perfect for SHU or Fairfield families staying in the area. Hope to visit again.

Pet-friendly home rentals with a pool

Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite
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 favorite
Apartment in Burlington
4.85 out of 5 average rating, 110 reviews

Charming apartment with breathtaking view!

AshleyRating, 5 stars2 weeks ago
Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!
Guest favorite
Guest suite in Holmes
4.98 out of 5 average rating, 194 reviews

Prvt pool Huge, Eclectic space… 1.5 hr to NYC!

PatriciaRating, 5 stars3 weeks ago
Blake is a kind and attentive host. The house is fun and eclectic. Many interesting things to look at, art books to leaf through and she has a great record album collection. It has all the necessities you would hope to see in an airbandb. I like the location. We enjoyed taking a hike in Mount Beacon park to see the remnants of an old casino and great views of the Hudson Valley.
Guest favorite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 181 reviews

Eco Cottage in the Woods

KymRating, 5 stars1 week ago
The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!
Top guest favorite
Cabin in Red Hook
4.96 out of 5 average rating, 352 reviews

Modern Upstate Cabin, near Rhinebeck NY

EllieRating, 5 stars2 weeks ago
We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.
Top guest favorite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars2 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.
Guest favorite
Apartment in Glastonbury
4.89 out of 5 average rating, 438 reviews

Quiet 2 bed room apt w/ private entrance.

JoshRating, 5 stars3 weeks ago
Alice’s place was great! We’ll be back again for sure.

Private, pet-friendly home rentals

Guest favorite
Home in New Milford
4.96 out of 5 average rating, 92 reviews

The Getaway: Beautiful Waterfront - New Milford CT

RosemarieRating, 5 stars2 weeks ago
Enjoyed our stay in the woods with a beautiful view of the river. Easy to get to and very close to the charming town of New Milford and many good restaurants. Although right off a busy road it was quiet inside the house. The great room, which is on the top floor, is wonderful and perfect for both working and entertaining and has a full bath. It looks like the photos with an amazing view. The bedrooms and another bath are underneath. The master bedroom is the best. Just be aware you can hear the footsteps from above and not all of the bedroom windows have bug screens. The entertainment room on the lower level which opens into the yard is filled with games and a large tv and was lots of fun. The weather was cool & rainy so we didn’t use the outdoor space as much as we thought we would but there was a kayak. The house was private and although there is no interior deadbolt we felt safe. The house was clean with good heat/ac and wi fi. Hosts were responsive.
Guest favorite
Home in Bridgewater
5 out of 5 average rating, 31 reviews

The Art House: 5-Acre Getaway w/ AC & Firepit

LisaRating, 5 stars1 month ago
Lovely stay at Jon's place. The house was very clean, great attention to details, and extremely comfortable beds. The outdoor fire pit patio is perfect or sunset viewing. The hosts were very responsive.
Guest favorite
Home in Woodbury
4.89 out of 5 average rating, 66 reviews

Historic Country Retreat in Litchfield County

TiffanyRating, 5 stars3 months ago
My family absolutely loved our stay! The home has been beautifully restored and is comfortable and clean. It was the perfect quiet getaway we were hoping for, while being close to all conveniences such as grocery stores, restaurants and coffee shops.
Superhost
Home in Watertown
4.8 out of 5 average rating, 44 reviews

Cozy Cottage

KatieRating, 5 stars2 weeks ago
This was the perfect place to relax after visiting family all day. Hector's place was clean, private, and peaceful. the drive way is a little hard to find but GPS will get you there fine. The airbnb had everything we needed and loved the back deck for grilling. highly recommend.
Top guest favorite
Yurt in New Milford
4.96 out of 5 average rating, 85 reviews

Yurt at Finnegan’s Farm, West

AndrewRating, 5 stars2 weeks ago
Amy and Bill’s hospitality was exemplary! The yurt is a well-thought-out structure — a definite step up from camping in the woods, offering a perfect mix of comfort and nature. The animals on the farm are beautiful and adorable, and they really add to the experience of the entire stay. There are plenty of little towns within driving distance where you can pick up whatever you need to cozy up at the farm. We’d love to stay there again if we get the chance!
Guest favorite
Guest suite in Sandy Hook
4.95 out of 5 average rating, 92 reviews

Light and airy, pet friendly rental in Newtown

BrieRating, 5 stars2 weeks ago
Suzanne’s air b&b was wonderful! The space was very clean and well taken care of. Also was a thoughtful gesture to provide a towel designated for wiping our dog’s paws! She was very great to communicate with as well. Would highly recommend! Thank you!
Guest favorite
Cottage in Seymour
4.93 out of 5 average rating, 55 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

JamieRating, 5 stars6 days ago
My family and myself loved every square inch of this property! From the serene views and well landscaped garden, to the sound of a stream to fall asleep to, the spotless interior and attention to detail…the pet bowls and bed, the labeled cabinets, the toiletries and games, we never wanted to leave! We last minute had to accommodate family members to be picked up later than the check out time and Michael was kind enough to extend our stay until 2pm so we could relax and enjoy more time together! We might make an annual trip out of this house and can’t thank the host enough for his immediate responses and making us feel right at home. Beautiful home, we loved sharing it! The first night we ate at the near by restaurant on the water, Housatonic House, also a recommendation on the fridge! Great food and service and BEAUTIFUL views! It ended up raining Saturday, but we still got a Hike in on our last morning at Osbornedale State Park, beautiful trails and picnic areas! Wonderful time.
Superhost
Cabin in Roxbury
4.88 out of 5 average rating, 16 reviews

Roxbury Cabin Retreat

Christopher TyRating, 5 stars1 week ago
Great quiet place for the family. Easy access to everything while still feeling secluded and restful

Destinations to explore