House vacation rentals in Chester

We booked a last minute stay at Matt’s airbnb - and we have zero regrets! The space is so clean, nice, and exactly what the pictures showed! The kitchen was stocked with spices, coffee, hot cocoa, and tea. The televisions were so nice with the high definition! There were fans in our rooms that we were able to plug in which was super thoughtful! It was such a quiet and peaceful area which made our little getaway perfect, you can even hear the running water from the outdoors if you open your window! Matt was very responsive and even checked in with us- which really stood out to us! We loved staying there so much we recommended it to our family who is coming to visit - they immediately booked their stay! We can’t say enough great things about Matt and his charming airbnb. We absolutely will stay here again!

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

It’s hard to express how beautiful the area is. The rambling old farmhouse fit our big family fly-in perfectly. This isn’t a place for folks who need everything polished & perfect, but it IS a place for a big crew to spread out, play games, and have adventures (do protect yourself from ticks if you venture into the woods). Kitchen was very functional for prepping big meals. Hot tub was a nice respite after long travel & rainy days. Lots of comfy nooks for solo time, reading, art-making as well as big gathering spaces for family meals. It’s a bit out of the way, but only 15 mins to grab groceries or supplies. Amazing getaway!

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!

We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Beautiful, historic home in a lovely neighborhood close to downtown Keene. Charming and cozy inside and out. Comfortable beds and furniture. Wonderful artwork by Ruth throughout her home. Large bright kitchen with everything you’d need to stay. Enjoyed the architecture and restaurants in Keene. Highly recommend Ruth’s home to stay in this area!

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

We enjoyed our stay immensely! We visit Rutland often and will continue to stay here as long as it is available! Everything was better than anticipated!

We had an amazing family ski weekend at this house! With four young children, finding a place that accommodates everyone can be challenging, but this house was perfect. It had two cribs, which was a huge bonus for us. The open floor plan made it easy to keep an eye on the kids while still enjoying time together as a family. The hot tub was a great way to relax after a day on the slopes, and there was plenty of space for our entire group to spread out and feel comfortable. The location was also fantastic—just a short drive to Mount Sunapee, making it so easy to hit the slopes. We couldn't have asked for a better place for our weekend getaway!

The house was perfect for our family weekend! The kids loved all the games and the fire pit! The kitchen was well stocked! The property is wonderful; very peaceful with the babbling brook and songbirds! Check in was so easy! Highly recommended!

Very responsive host who went above and beyond to display hospitality. Clear instructions and let us enjoy the place in peace. Space itself was warm and inviting and perfect for a couple's weekend away.

We had a great stay here! It was simple and exactly what we needed, we’d definitely stay here again in future trips to Keene!

This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!

It was a great two week stay.. I enjoyed being at this lake house. The lake is across the road, and pretty to look at on the balcony. The clear view of the lake walking and driving in the morning was very peaceful. His dock is the nicest in comparison to his neighbors. Kitchen was very well equipped, top notch washer and dryer, excellent lighting , beds and linens were comfortable, couch was large, easy to sprawl out and take a nap. Michael was available and easy to communicate. The high reviews are true, he cares and is thoughtful . I look forward in future stays .

We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay again.

Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

It was perfect for my overflow guests attending a weekend family reunion!

Great house, amazing location near Stratton, and Matthew was just great. He was super communicative, and went above and beyond to make sure we were happy with our stay. We'd love to return again.

Went here with a large group of friends for a skiing trip in Killington and the location and house was perfect for what we needed. Herb was extremely responsive to all questions and concerns we had, would absolutely recommend staying here if your a skier/border or are just trying to experience the area with a large group of people!

Our stay at Mian and Anthony ’s place was fantastic! The house was impeccably clean and well-stocked with everything we needed. Mian and Anthony were very accommodating and provided great local tips. If we ever find ourselves back in the area we will definitely stay here again.

Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.

Our family of five just spent Thanksgiving at the lake house. Its size and layout accommodated us well - having the second frig became necessary. It’s a lovely place and stunning views from almost every window. Would definitely come again. Thanks!

Surrounding area was very peaceful and the wrap around porch was a great way to see the nature. We loved the wood burning stove. Eccentric details and the space felt lived in.