Pet-friendly vacation rentals in Chester

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!

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.

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!

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.

We had a wonderful weekend in Vermont! The Airbnb was beautiful, clean and in a great location!

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!

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!

Dreamy! The property is not to be believed. On top of the scenery itself, a grill, hot tub, sauna, fire pit, pond-side hammock, and disc golf (a pleasant surprise)—what more could you ask for.

Even in the rain, this was the perfect getaway! A mix of summer camp and mountain cabin vibes made it feel warm and welcoming

Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

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 cabin was lovely! We went for a little weekend getaway with some friends and it is a great space for such an occasion. There is a surprising amount of space in and around the house and we didn't even use the three season porch. The hosts were also very responsive and easy to communicate with. Definitely a cute little home away from home!

Great stay and was exactly what we needed for our entire family for a weekend wedding!

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.

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.

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!

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!

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.

Danielle and Ben were excellent hosts and their guide was really helpful and informative for us who had never been to Vermont or the area! We really enjoyed spending time in the location and it was only made better by returning to their beautiful and peaceful home. The place is even better than the pictures, everything was exactly as described, and we had plenty of spaces to choose from for alone time and gathering time with our group. Danielle and Ben remained communicative throughout and proactive with info we needed for check-in. We will certainly be back to Vermont and we know exactly the place to go for the most elevated and serene experience possible. Thank you!!

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.

The view simply amazing. George our host was and he is all the things a good host should be; welcoming, helpful, accommodating, great personality and an awesome dog as well. I will strongly recommend this location if staying on top of a mountain with great views and a warm shower sounds like a great day to you. We stayed in the main cabin and it had everything we needed and then some. Very cool vintage design feel and very clean. Great job George! We will be back!

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.

Susan and Carmen's place was just as advertised. We really appreciated their flexibility on check-in and it was nice meeting Carmen to show us around. The space is very cozy and comfortable. The cabin is well equiped with all the items you need for a stay, as well as some toys that my young daughter enjoyed playing with. There was a sulfur smell with the hot water, but I know Carmen is working to resolve that and we were told the water is safe to drink. Beautiful views and close to Magic MTN and Ludlow. I'd love to stay there again.

Great house and location to bring family and friends for a ski trip getaway! Very responsive and attentive host. Had a wonderful stay.