Pet-friendly holiday 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 favourite
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 favourite
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 favourite
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 favourite
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!!
Guest favourite
Home in Grafton
4.94 out of 5 average rating, 120 reviews

The Grafton Chateau

EmmaRating, 5 stars3 months ago
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.
Top guest favourite
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 favourite
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 favourite
Home in Cavendish
4.93 out of 5 average rating, 104 reviews

Renovated Vermont Schoolhouse – Close to Okemo

ChrisRating, 5 stars3 months ago
Marianne was so responsive and kind. The place is super close to Okemo. The space is probably bigger than it looks like in the photos. Super quiet secluded spot. Kitchen was nice and big for us to cook for a troop of hungry skiers. Thought this was a really nice family oriented spot. Second time we have stayed there and hope we can come back there for more ski trips!

Pet-friendly home rentals with a pool

Guest favourite
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
Top guest favourite
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 favourite
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 favourite
Apartment 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.
Guest favourite
Apartment in Killington
4.94 out of 5 average rating, 258 reviews

AC/Dog-Friendly/Spa Onsite/Pool/Wine Bar

ErinRating, 5 stars4 weeks ago
The Woods complex is a peaceful retreat style community. The condo is cozy with fresh, on point decor. The kitchen was a bit tighter than expected but has generous countertop space. The hosts are friendly and responsive. The stairs to get to the condo could be difficult to navigate for people with mobility restrictions.
Top guest favourite
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
Apartment 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 favourite
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 favourite
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!
Guest favourite
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.
Guest favourite
Cabin in Woodstock
4.95 out of 5 average rating, 200 reviews

Hideaway Cabin by the Stream on 27 Acres

JenniferRating, 5 stars2 weeks ago
Our stay was incredible! The view by the stream was amazing, everything was so peaceful and perfect. Inside the cabin was exactly what we expected, very homey, everything we needed. We loved the walls lined with books! Kevin was very attentive towards what we needed - it stormed all day Saturday and he brought a second heater for us because the temperature dropped, which with that and the gas fireplace, kept the place perfectly warm and comfortable. He was also very accommodating in allowing us to stay an extra night since our plans of hiking all weekend were thwarted by the rain. We went for my husband's 40th birthday and i couldn't have picked a better place to get away from the stress of life. We plan on going back for sure!
Top guest favourite
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.
Guest favourite
Cabin in Fort Edward
4.95 out of 5 average rating, 316 reviews

Farm Stay! - 20 min from Lake George-30 Saratoga

JennaRating, 5 stars5 days ago
Our cabin was cute and the kitchen cabin next to it made everything so spacious and nice. The shower was warm and just what we needed on a long road trip plus the bed was comfy as comfy can be.
Top guest favourite
Barn in Marlboro Township
4.96 out of 5 average rating, 315 reviews

The Studio With a View. Bring your dog, too!

AmandaRating, 5 stars3 weeks ago
We had such an amazing stay at the studio! The place was beautiful and clean. Nicole had awesome recommendations on things to do and they even had toys for our pup that we brought along. Would absolutely stay again and would recommend it to everyone!
Top guest favourite
Farm stay in Croydon
4.98 out of 5 average rating, 161 reviews

Lighthouse Inn the Woods~peaceful farmhouse stay

MariahRating, 5 stars2 weeks ago
Our third time staying at the farm and it truly only gets better and better every time. This place is absolutely gorgeous, pictures really don’t do it justice. The house is so adorable and clean not to mention Frankie and Vin pay insane attention to detail and have thought of literally every single thing you might need during your stay and are just some of the all around best people. There’s so much to do weather you go out and explore the property stopping to say hello to the animals and give them treats, hike the near by trails, or simply just staying in playing games and listening to music on the record player you can’t go wrong staying at Frankie and Vins!
Guest favourite
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!

Quick stats about holiday rentals that are pet-friendly in Chester

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹10,331 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

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Chester
  6. Pet-friendly rentals