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 Fairlee
4.96 out of 5 average rating, 506 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

DianaRating, 5 stars2 days ago
The Bow house was a beautiful place and Jen was incredibly hospitable and responsive. This is an amazing place to come and get away from the noise. Everything was so clean and cozy. Would definitely come again!
Guest favourite
Home in Barnard
4.99 out of 5 average rating, 147 reviews

The Looking Glass, a modernistic escape

MonikaRating, 5 stars1 week ago
I booked this spot for my birthday/ mother & daughter getaway and was not disappointed! The views were great and the whole place was very relaxing. Angela was quick to respond to any questions that we had. We traveled with my 3 year old rescue dog and he had the time of his life. There was plenty of space for him to run around! We will certainly be back!
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
Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Top guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month 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!
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 stars1 month 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.
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 stars2 days 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!
Top guest favourite
Guest house in Salem
4.97 out of 5 average rating, 108 reviews

Guest House at Hummingbird Hill

AmyRating, 5 stars1 month ago
Lovely place. A private separate building on a family property. We rushed in and out because we were there for a bike race, but I really wanted to stay longer and enjoy the space. I loved the two chairs set out in a tree shaded area. The bed was comfortable, the place had real charm, and Melissa was around and responsive.
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, 26 reviews

Scandinavian Serenity Close to Okemo

ColleenRating, 5 stars2 days ago
We adore this perfectly peaceful getaway in VT! This was our third stay at the Scandanadian oasis and for anyone visiting VT, you have to see it in June! So many beautiful flowers in bloom decorating the property. Yulia and Mark were absolutely wonderful and responsive. The house is always immaculate! Highly recommended!
Guest favourite
Guest house in Londonderry
4.93 out of 5 average rating, 196 reviews

Beautiful Guest House near Bromley, Magic, Okemo

AnneRating, 5 stars1 month ago
Truly a beautiful, serene, contemplative guest house. We loved its simple beauty, the artistry and character of the furniture and the exquisite natural beauty surrounding this lovely place. We felt right at home and were so appreciative of Scott's thoughtfulness in setting the inside temperature to warmly welcome us upon our arrival. Vermont has always held a special place in our hearts and this experience endeared us even more to the beauty, serenity and simplicity that is so abundant and always nourishes our hearts, and souls and bodies - whenever we have a chance to visit.
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!

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    $154 SGD 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