Holiday rentals with outdoor seating in Chester

This place was exactly what we were hoping for — clean, peaceful, and just as described in the listing. The space was beautifully designed, with thoughtful touches throughout, and everything was in great condition. It felt cozy and inviting from the moment we arrived. Communication with the host was smooth and easy, and check-in was a breeze. No surprises — just a really great stay in a beautiful part of Vermont. I’d absolutely come back again.

Thank you, Bianca, for a wonderful stay in your stylish, clean, comfortable home and beautiful property. We would definitely rate it five stars and highly recommend it to others. An extra thank you for accommodating our unplanned family graduation dinner—it meant a lot to us! Sergey and Taya

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!

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!

We had such a wonderful time in New Hampshire thanks to Melora! The house was exactly what we were looking for. The views of the lake were to die for!

A great stay at the Lake House. Gorgeous views, fully stocked kitchen, and canoes/SUPs/kayak for everyone. Andrew was very responsive and a great host. We hope to return soon!

We were in the area for a wedding and this was a perfect alternative to the hotel options. A beautiful house - we would definitely stay here again.

Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

William is an excellent host and his place is wonderful. I’ve stayed with him. Multiple times. Recommended!

I made the right decision when I chose to stay at Jaki's place. The kitchen was fully equipped so that I could prepare my meals at home and the private deck was a bonus. The location was quiet and felt tucked away, while only being a five-minute walk to downtown. The check-in process was super easy and Jaki made it her priority to ensure I had everything I needed for a pleasant stay.

We had a great stay at the HeART Barn and will definitely be looking to book again in the future! Such a beautiful, comfortable, and homey space located on a beautiful property. Brianna is incredibly kind as well. Highly recommend!!

Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

This cozy apartment in a beautiful, quiet setting is conveniently located close to NECCA and Brattleboro. Millicent and Tony provided numerous thoughtful touches, like local maple syrup in the fridge! They clearly care about the comfort and convenience of their guests, and were even upgrading the walkway lighting while we were there. The gardens right outside our large windows were in full bloom, and we woke to bird songs. I look forward to returning!

Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!

Clean, great location, easy check in/out, and friendly host - would definitely stay again.

This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

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

Couldn’t have asked for more. Cozy, clean and such a comfortable place to stay and exactly what was described in the listing. I’ll certainly be booking again! Tricia’s communication was perfect, everything very clear and didn’t have to reach out with extra questions.

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

⭐️⭐️⭐️⭐️⭐️ Perfect Father–Son Getaway at CozyCub! My son and I stayed one night at the CozyCub condo in Killington, and once again, Dan and Holly delivered a flawless experience. From the moment we arrived, everything was spotless, cozy, and thoughtfully arranged—exactly what we look for in a mountain bike trip base. Comfort & Cleanliness: The condo was pristine, with comfy beds and fresh linens—like a home away from home. Attention to Detail: Every essential was readily available, from kitchen basics to crisp towels. Perfect for a Duo: Ideal layout and amenities for just the two of us—no waste, just well-tailored space. Consistent Excellence: We’ve stayed with Dan and Holly before, and CozyCub continues to meet our high expectations. This stay earned a full five stars. Thanks again to Dan and Holly for providing the perfect retreat—we’ll be back for our next biking adventure together!

We loved staying at this cozy condo. We were able to find it easily and get inside without any issues. The bed was the best we’ve encountered in an Airbnb! I loved the small creek behind the condo and sitting on the balcony with my tea listening to it was a wonderful way to start the day. We would definitely come back again.

It was such an easy check in and check out process. He let us check in an hour early since we arrived earlier. Place is spacious and exactly as described. Highly recommend!