House vacation rentals in Chester

Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there 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!

Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!

Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay 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.

Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

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.

Beautiful home. Pictures don’t do this location justice. Booked for our daughters wedding being held close by for relatives traveling and ourselves to be close to wedding. Would highly recommend for anyone looking in that area. They have thought of everything you could possibly need. We were out at events more than at the home and I honestly with we had done another day to enjoy some down time in the beautiful home. Owners and local property manager were wonderful at communicating and making sure everything was cared for (we had no concerns, but having contacts if there were any)

Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy

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.

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!

Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.

This place is great! Exactly as described inside, clean & well-appointed home. Everything is labeled very helpfully and all amenities were available and clean. Hot tub is inside a sweet little screen tent that allows for extra privacy which is much needed as the next door neighbors are very visible/present next to the outdoor space. The washer and dryer were new, the fridge was very new and had an awesome ice dispenser with 2 types of ice it automatically created. Don't let the house rules shy you away. This host is through but very kind and professional. The only downside of the entire place is a rather complex air conditioning/heating system that I found diddicult to understand but also made it uncomfortably hot throughout the night and there are signs everywhere instructing not to open the windows at all which was odd. Overall this place is so worth it, if you're staying in Keene and need a larger space, this place is perfect.

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!

This is a place that gives families the time, simplicity, and space to relax together and reconnect. All of the happiness and love of many generations fills the air. This is a wonderful setting for extended families and friends to gather. There is a lot for everyone to do at the house, the lake, and in the Monadnock region. This is a one of a kind property that is very special today more than ever.

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.

Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.

The overall experience is good. Just a reminder: the 1st and 2nd floors use separate doors and are not internally connected. However, the location is very close to Okemo and Killington, and the interior decoration is quite good for the price.

Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks 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.

Great spot for a week of skiing! Danielle was very helpful and communicative throughout