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, 192 reviews

Vacation Home In Millerton

VictoriaRating, 5 stars1 day ago
The house was perfect for our stay, our daughter had reunion at Hotchkiss. We were able to visit and catch up with her friends and families and others from Hotchkiss, great location great gathering spot in the kitchen at the table !
Guest favorite
Home in Fairfield
4.96 out of 5 average rating, 149 reviews

Top Rated Gem | Fire Pit | Near Beach, FFU & SHU

DavidRating, 5 stars2 weeks ago
Claudia is a wonderful and responsive host, who sent us helpful information and recommendations of area restaurants. Her home is so cozy and immaculate, with special touches throughout. It’s also in the heart of Fairfield, within minutes of anywhere in town. We’ll certainly be back!
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, 155 reviews

Nature Cottage w/ Private Path to River Access

ErnestRating, 5 stars2 weeks ago
This house was perfect for us (5 friends gathering to fish the Housatonic). Simple, clean, ac/heat/wood-burning stove, all the amenities, and a great hot shower! We were up and down the short path to the river the whole weekend. Amy was a super-host. Attentive when we needed her, but not intrusive. Thanks Amy, we enjoyed our stay!
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars2 weeks ago
Only complaint would be the noise from road during the morning commute
Top guest favorite
Home in Milford
4.99 out of 5 average rating, 111 reviews

The ARLO - Walk to Brewery & Restaurants

LaurieRating, 5 stars1 week ago
The ARLO was super cute and very clean. It had ALL the amenities we needed. Outstanding communication with the hosts. Great welcome guide full of info. that answers all your questions. Looking forward to coming back 💕
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 starstoday
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 favorite
Farm stay in Red Hook
4.99 out of 5 average rating, 157 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

MaryRating, 5 stars2 weeks ago
Peaceful and charming stay in Rhinebeck. The farmhouse was cozy, and the kids loved watching the goats and turkeys roam. A perfect little reset while antiquing.
Guest favorite
Guest suite in Holmes
4.97 out of 5 average rating, 195 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, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

JenniferRating, 5 stars1 week ago
Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.
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.

Private, pet-friendly home rentals

Guest favorite
Home in New Milford
4.91 out of 5 average rating, 93 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, 32 reviews

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

BaileyRating, 5 starstoday
My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!
Top guest favorite
Home in Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!
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, 94 reviews

Light and airy, pet friendly rental in Newtown

DawnRating, 5 starstoday
Suzanne’s place was spotless! I stayed here one night with two of my daughters and we were very comfortable. We got in later than expected, from a family graduation, and Suzanne was very kind and quick in responding. Her place is in a quiet, peaceful neighborhood. We also liked her local guide and went to Caraluzzi’s market for groceries. Thanks for a great stay!
Guest favorite
Barn in Roxbury
4.97 out of 5 average rating, 39 reviews

Classic Red Barn with game room

JulietRating, 5 stars3 months ago
This was the second time I stayed at Vicki's gorgeous place. Vicki's is 8 minutes from my sister's house and if all goes well I will always stay at Vicki's when I am visiting as it's such a lovely place and so convenient while giving me and my partner the privacy we want when visiting extended family. Vicki's apartment is cozy and extremely clean and beautifully decorated in a modern/country style that I love.
Top guest favorite
Guesthouse in Morris
4.96 out of 5 average rating, 50 reviews

Peaceful Year Round Lakehouse

BrunoRating, 5 stars3 weeks ago
Ellen is a truly outstanding host—kind, responsive, and genuinely committed to making sure you have a wonderful stay. She goes above and beyond to help make your vacation special. The house is perfect for families with young kids who love nature and want to unwind while having fun. It’s well-equipped with everything you need to feel at home, thoughtfully decorated, and filled with entertainment options. One of the highlights is the access to a private lake beach and what my 5-year-old proudly declared “the best swing ever.” There are also great little nature trails to explore right on the property. Don’t think twice—book this place. You won’t regret it!

Destinations to explore