Pet-friendly vacation rentals in Chester

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Chester pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Barnard
4.99 out of 5 average rating, 146 reviews

The Looking Glass, a modernistic escape

SandyRating, 5 stars2 weeks ago
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.
Guest favorite
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.
Guest favorite
Home in Winhall
4.95 out of 5 average rating, 141 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

DoxiaRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Danby
4.96 out of 5 average rating, 227 reviews

Comfortable farmhouse with stunning views

CarterRating, 5 stars1 month ago
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!!
Top guest favorite
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!
Top guest favorite
Home in Poultney
4.92 out of 5 average rating, 123 reviews

Cozy Home in Poultney, Vermont.

DanielRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Weston
4.96 out of 5 average rating, 236 reviews

Weston Farmhouse-Clean, Fast WiFi, Generator!

JustinRating, 5 stars2 months ago
great home base to enjoy Okemo and the surrounding mountains. super spacious, clean, and comfortable. Kim was a great host!
Guest favorite
Home in Mount Holly
4.92 out of 5 average rating, 119 reviews

Backyard River Fun & Arcade!

BingRating, 5 stars2 months ago
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

Guest favorite
Tiny home in Brattleboro
4.93 out of 5 average rating, 121 reviews

“Elm” Cozy Pond-side Cabin w/wood stove

MollyRating, 5 stars3 weeks ago
Even in the rain, this was the perfect getaway! A mix of summer camp and mountain cabin vibes made it feel warm and welcoming
Guest favorite
Condo in Killington
4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

CarlaRating, 5 stars2 weeks ago
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.
Top guest favorite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars4 weeks ago
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!
Guest favorite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Top guest favorite
Condo in Killington
4.99 out of 5 average rating, 101 reviews

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

WesRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Newfane
4.99 out of 5 average rating, 234 reviews

Cozy Vermont Antique Sugar House with Fireplace

ArielRating, 5 stars1 week ago
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.
Superhost
Condo in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars5 months ago
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.
Guest favorite
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!

Private, pet-friendly home rentals

Guest favorite
Tiny home in Chester
4.93 out of 5 average rating, 41 reviews

Sage House at Camp Greenwood Vermont with Sauna

SuriRating, 5 stars1 day ago
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!
Superhost
Guest suite in Weston
4.97 out of 5 average rating, 220 reviews

Spacious King Spa Suite Weston Hills

StephanieRating, 5 stars3 months ago
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!
Guest favorite
Cabin in Chester
5 out of 5 average rating, 10 reviews

Cozy Mountain Cabin | Fireplace | Secluded Getaway

LaurenRating, 5 stars4 months ago
Super cute, clean, and cozy cabin in a peaceful, remote location. Hannah was an especially responsive and accommodating host. Would definitely stay there again!
Guest favorite
Cottage in Chester
4.9 out of 5 average rating, 96 reviews

Quaint stone house!

RachelRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Springfield
5 out of 5 average rating, 25 reviews

Scandinavian Serenity Close to Okemo

RioRating, 5 stars2 months ago
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.
Top guest favorite
Chalet in Jamaica
4.98 out of 5 average rating, 260 reviews

Vermont Chalet

KimRating, 5 stars1 week ago
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.
Guest favorite
Home in Chester
4.95 out of 5 average rating, 42 reviews

Beautiful farmhouse in Historic village

LaineRating, 5 stars5 months ago
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!
Superhost
Home in Town of Rockingham
4.63 out of 5 average rating, 43 reviews

Simple 2+ bed, no frills, all necessities covered!

MuditRating, 5 stars7 months ago
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

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  4. Windsor County
  5. Chester
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