
Pet-friendly vacation rentals in Chester
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Top-rated pet-friendly home rentals in Chester
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Pet-friendly house rentals

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

The Looking Glass, a modernistic escape
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!

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!!

The Grafton Chateau
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.

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!

Renovated Vermont Schoolhouse – Close to Okemo
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

“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

Magical Farm Getaway - a must visit!
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!

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.

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

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.

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!

Guest House at Hummingbird Hill
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.

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.

Hideaway Cabin by the Stream on 27 Acres
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!

Scandinavian Serenity Close to Okemo
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!

Beautiful Guest House near Bromley, Magic, Okemo
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.

The Studio With a View. Bring your dog, too!
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 vacation rentals that are pet-friendly in Chester
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ441 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
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- 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
- Ekwanok Country Club
- Bretwood Golf Course
- Hooper Golf Course
- Brattleboro Ski Hill
- Veterans Memorial Recreation Area Ski Hill
- Fox Run Golf Club