
Pet-friendly vacation rentals in Chester
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chester
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester pet-friendly home rentals
Pet-friendly house rentals

The Looking Glass, a modernistic escape
Overall we very much enjoyed modern rural space. Kiss the Cow farm about 5min drive was amazing& we got most all main food there w/ additional items from Barnard General Store. Spices/ cookware were very good - we brought nonstick pans& 1 knife to supplement. Plenty bowls, measuring cups/spoons, maybe a set of tom collins glasses would be nice albeit stemless wine and rocks glasses available. Needs garlic/onion powder. Tub was amazing/ upstairs bathroom a true getaway/ relaxing space. It was as pictured albeit note spiral staircase &open grated flooring upstairs. Plenty of windows albeit not much cross breeze so think ahead if bring own fan and/or start A/C before get too warm. I would say you must have an SUV year round for this rental - surrounding roads/ driveway are a good distance on rough dirt/gravel - traversable yet a sportier car with low profile tires/ ground clearance would not work. We enjoyed simply walking driveway& East Barnard Rd. Barnard Inn restaurant worth it.

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.

Summit View Ski and Golf Retreat w/hot tub & Sauna
The home is gorgeous - thoughtfully decorated, cozy and clean. The location is perfect for access to Stratton and to Manchester. The host, Jason, provided very clear and helpful instructions for check-in, check-out and use of the home and is friendly and attentive. This is a wonderful place to stay!

Comfortable farmhouse with stunning views
Such a cool house. We loved the charm of the older section of the house. So many private spaces to cozy up and read a book. Then there is the more modern portion of the house. It was perfect for the folks to watch tv and enjoy the VT scenery out of the large windows. The road is quiet and the area is lovely. We easily drove into Manchester for groceries and dinner. Really loved it!!

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

Cozy Home in Poultney, Vermont.
The space was fantastic for our two little families with easy access to the local Slate Valley Trails. Lots of wonderful and attentive touches to make our stay homey welcoming. Hope to return again soon!

Weston Farmhouse-Clean, Fast WiFi, Generator!
great home base to enjoy Okemo and the surrounding mountains. super spacious, clean, and comfortable. Kim was a great host!

Backyard River Fun & Arcade!
Christine’s place is easy to find and conveniently located near Route 103, a major road in Vermont. Despite its proximity, it remains quiet, especially at night. The house is very close to Okemo, making it a great choice for a ski weekend. There’s plenty of parking, and the home is well-equipped for a short stay, with lots of games to enjoy. It’s also clean and well-maintained. Christine is a proactive and attentive host, providing helpful information before arrival and checking in during the stay to ensure everything goes smoothly. Highly recommend!
Pet-friendly home rentals with a pool

“Elm” Cozy Pond-side Cabin w/wood stove
Even in the rain, this was the perfect getaway! A mix of summer camp and mountain cabin vibes made it feel warm and welcoming

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Ranch at Mendon Mt Orchards
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
We had a wonderful stay at this Air Bnb. A lot of privacy and full access to any amenities that we needed. Everything was up to date and well put together. Our only issue was someone was walking around with a flashlight late at night, not sure if it was a security guard or whatnot but they got into our backyard and around the house so it seemed a little off. Other than that it was everything we wanted.

Cozy Vermont Antique Sugar House with Fireplace
Lenore's place was very cozy. We felt right at home. We added guests (including a dog) after initially making our reservation and it was no problem with the host. Just a note, it costs a fee to add more guests on Airbnb. Overall our stay was lovely and our hosts were very nice, responsive, and welcoming. 10/10, would recommend.

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.

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!
Private, pet-friendly home rentals

Sage House at Camp Greenwood Vermont with Sauna
We went up to the area for 2-day wedding and this was such a great option for relaxation and restoration in between events. Thanks so much for a wonderful weekend!

Spacious King Spa Suite Weston Hills
Denise’s place was beautiful! It was private and quiet which helped our dogs settle in and helped my husband and I relax after 2 days of skiing. The bathroom….enough said. Absolutely stunning - the pictures don’t do it justice! It was thoughtful of Denise to have some fruit and breakfast items provided in the fridge like creamer, OJ, and bagels w cream cheese. This is a perfect getaway for a couple, I would stay again and I highly recommend!

Cozy Mountain Cabin | Fireplace | Secluded Getaway
Super cute, clean, and cozy cabin in a peaceful, remote location. Hannah was an especially responsive and accommodating host. Would definitely stay there again!

Quaint stone house!
We had a long weekend at the cottage and loved our stay. The house was warm and welcoming and offered a lot to do inside and out. We appreciate the care that was obviously put into making the space so special.

Scandinavian Serenity Close to Okemo
It's possible I've never given 5 stars and checked every chip for an airbnb. This space was absolutely stunning. Such beautiful and peaceful surrounding, loads of clean and comfortable towels, the most comfortable beds (if you like firm beds), the sauna was amazing and smelled so good too, the host was responsive, flexible, friendly, and accommodating, and the interior design and comfort of the home because of its lighting, games, kitchen, living space... just everything, absolutely pristine.

Vermont Chalet
Beautiful large A frame home in the middle of a lush forest. Everything was comfortable and felt like a well loved family vacation home (not one of those sterile investment only properties). Kitchen was incredibly well stocked and host even left a bottle of wine. Gorgeous orange newts emerged in the yard when it rained. If you’re looking for a peaceful retreat, this is a great spot. It is a bit of a drive to get anywhere, and there’s no cell service for a while in several directions, but the wifi worked great. Just download directions and maps before leaving the house.

Beautiful farmhouse in Historic village
This was a great place to stay for skiing at Okemo! The house is so spacious, has enough room for everyone! We loved the large dining table for dinners. Would stay here again!

Simple 2+ bed, no frills, all necessities covered!
Great place, especially for the budget. It was clean, comfortable, and had everything we needed for a relaxing stay.
Quick stats about vacation rentals that are pet-friendly in Chester
Total rentals
20 properties
Nightly prices starting at
G$25,098 GYD before taxes and fees
Total number of reviews
910 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Boston Vacation rentals
- Hudson Valley Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Pocono Mountains Vacation rentals
- Jersey Shore Vacation rentals
- Québec City Vacation rentals
- Philadelphia Vacation rentals
- Rentals with outdoor seating Chester
- Rentals with a patio Chester
- Family-friendly rentals Chester
- Rentals with a fire pit Chester
- Kid-friendly rentals Chester
- Rentals with a fireplace Chester
- House rentals Chester
- Rentals with a washer and dryer Chester
- Pet-friendly rentals Windsor 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
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Autumn Mountain Winery
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Clarksburg State Park
- Hooper Golf Course
- Brattleboro Ski Hill
- Bretwood Golf Course
- Fox Run Golf Club
- Ekwanok Country Club
- Veterans Memorial Recreation Area Ski Hill