
Pet-friendly holiday rentals in Chester
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Top-rated pet-friendly home rentals in Chester
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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!!

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

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.

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!

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
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.

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

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!

Lighthouse Inn the Woods~peaceful farmhouse stay
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!

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!
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
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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
- Hooper Golf Course
- Brattleboro Ski Hill
- Bretwood Golf Course
- Fox Run Golf Club
- Ekwanok Country Club
- Veterans Memorial Recreation Area Ski Hill