House holiday rentals in Chester

We really enjoyed our stay at this super cute Airbnb! The location was perfect — just a quick drive to everywhere we wanted to go, which made exploring the area super convenient. The space itself was clean, cozy, and had such a charming vibe. One thing to note is that there’s no AC, which I didn’t realize ahead of time. It wasn’t a dealbreaker by any means, but as a cold sleeper, it was a bit warm for me in June — just something to keep in mind depending on the season. Overall, it was a lovely place and a great spot for a getaway!

We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

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.

We had such a wonderful stay at this historic home! Ruth was a great host and was easy to communicate with, even when I needed to message her late at night. The rooms were great and it was in a perfect location. We are looking forward to booking here again next year.

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!! 🤩

9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!

Yulia and Mark's place is perfect for a getaway, so perfect in fact that it takes a little while to sink in. Located on a forested hill, the pristine mid-century modern house is quiet, calm, and restorative. Little by little, lovely details accumulate - like the glorious landscaping, the harmony of sloping roofs on outbuildings in synchrony with the bold and simple lines of the main house, the view of tall trees from each room - including bathrooms, the total quiet since the road nearby is hardly traveled. The place is full of lovely amenities and the sauna is a delight - even in heat and easy to use. Mark and Yulia were both quick to communicate and to help solve small problems, and we were lucky to meet Mark in person - wonderful and welcoming. We only wish we could have stayed longer. Next time...soon, I hope!

Our family had an incredible, 3 week, stay at Terri’s home in Chester, Vermont! From the moment we arrived, we felt right at home. Terri was a fantastic host -responsive, thoughtful, and always quick to assist. Her communication was excellent, making our stay seamless and stress-free. The house was beautifully decorated, warm, and inviting, with every detail carefully considered. It was fully equipped with everything we needed, and the beds were exceptionally comfortable. It’s even bigger and more beautiful than the pictures show! The cozy yet spacious layout made it perfect for relaxing after a day of exploring. The location was perfect—centrally located near so many attractions yet set on a peaceful, private property. It offered the best of both worlds: easy access to activities while providing a quiet retreat surrounded by nature. We can’t recommend this home highly enough! When we return to Chester, we will book again in a heartbeat. Thank you, Terri, for a truly wonderful stay!

Great communication- nice spot for our work trip. Would stay again!

This was our second time staying at the Mill House, and it was just as magical! Beautiful home with lots of historical details. Kids loved the hot tub after a day of skiing. Hoping to be able to visit again in 2026!

Great place, especially for the budget. It was clean, comfortable, and had everything we needed for a relaxing stay.

The house was roomy, clean and exactly as presented. Getting into the house was easy and we had no issues whatsoever. Very smooth experience all around!

Really lovely cabin with beautiful open design and decor. Reasonable drive to Magic Mountain and the surrounding area for skiing and other winter sport activities, and a great bathtub for your sore muscles afterward. Heat was super effective, hot water didn't run out even with four of us showering back-to-back, kitchen was well-supplied and there's a nice big driveway with plenty of room to park and turn around. There was even a closet full of boardgames; we played a lot of Scrabble. Of note — like much of Vermont, this is on a gravel/dirt road and it would be a bit sketchy to get there without good tires and four wheel drive. It also snowed a couple times while we were there and the stairs up to the house get very icy. So generally, if you're going in winter, be prepared.

The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

Beautiful, spacious house, just as described. Clear instructions and responsive hosts.

Great place! Right downtown near everything and super walkable. Nice rooms, clean and tidy! Would recommend, perfect for a weekend get away.

Exactly what was expected. Could it be better? Sure it could but really it was a nice large space that worked very well for our ski trip. Good, spacious kitchen. Nice bedrooms. Good wifi and enough outlets not to worry about anything.

Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

This is a wonderful retreat! The property offers excellent hiking from the doorway, including a rewarding walk to the hilltop. It is conveniently close to ski areas while maintaining a cozy, homey atmosphere that made us feel completely comfortable. We highly recommend it!

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

Julie’s place is fantastic. Great location close to the grocery store, downtown, and Okemo Mountain Resort. Awesome fireplace. Great kitchen. Gadgets for drying ski gloves/mittens and ski boots were very cool. Highly recommend!