Holiday rentals with a patio in Chester

My friend and I booked a stay here on Memorial Day weekend when it became clear our camping trip would be rained out. We had such a wonderful time at Dana’s place! The space was immaculate and the bedrooms were very comfortable. The skylights throughout provide natural light, which contributes to the calm atmosphere. Even though we weren’t able to camp, we were still able to make s’mores on the fire pit and got some great hiking in nearby. Dana was a wonderful attentive host, and provided great recommendations for things to do in the area. We would definitely return!

Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

We had such a wonderful stay at Peter’s place this weekend! It was one of the nicest Airbnbs we’ve ever stayed in. Very clean, cozy and super welcoming. We were so happy to be able to bring our pup along and the location was perfect. It was close to the lake and great local restaurants. The view from the deck was absolutely beautiful!

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

If you are in the Brattleboro area, I highly recommend this listing. It was clean, comfortable, and quiet. We were there for just one night, but were very pleased with these accomodations.

Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.

Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

Gabriella is a very responsive host. I appreciated her attention when we had questions or feedback. You cannot beat this place if you are a skier and the proximity of the location to the ski base and lodge! We immensely enjoyed our stay here even as novice skiers!

Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.

This house was the best ski weekend away! Conveniently located yet secluded for a peaceful stay. The home itself is spacious, charmingly rustic, and thoughtfully stocked with everything we needed—especially the fully equipped kitchen, which made cooking a breeze. The atmosphere was cozy and inviting, making it the ideal spot to relax and unwind. Highly recommend.

We had a terrific stay at the Sunrise Cottage during the Memorial Day weekend! Colleen is a superb hostess and was in constant communication with us whenever needed. She was flexible with check-in and check-out times for us. Her Cottage was very well stocked, very clean, very spacious, and had plenty of room for us, and my Brother's family. My niece stopped by with her 2.5 yr old daughter, and there were so many toys for her to stay busy with that she was in her glory keeping herself occupied. I would highly recommend the Sunrise Cottage and Colleen to anyone looking to stay around the Springfield area. It's in a great location! We will definitely look into staying there for future visits.

Overall we very much enjoyed modern rural space. Kiss the Cow farm about 5min drive was amazing& we got most all main food there w/ additional items from Barnard General Store. Spices/ cookware were very good - we brought nonstick pans& 1 knife to supplement. Plenty bowls, measuring cups/spoons, maybe a set of tom collins glasses would be nice albeit stemless wine and rocks glasses available. Needs garlic/onion powder. Tub was amazing/ upstairs bathroom a true getaway/ relaxing space. It was as pictured albeit note spiral staircase &open grated flooring upstairs. Plenty of windows albeit not much cross breeze so think ahead if bring own fan and/or start A/C before get too warm. I would say you must have an SUV year round for this rental - surrounding roads/ driveway are a good distance on rough dirt/gravel - traversable yet a sportier car with low profile tires/ ground clearance would not work. We enjoyed simply walking driveway& East Barnard Rd. Barnard Inn restaurant worth it.

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 was a perfect place for our group of 3 couples and 2 kids. Plenty of space, 15 min from Okemo for skiing and well-stocked for cooking in. We enjoyed the amazing stars from the hot tub at night! Brien and Victoria were super responsive and helpful.

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.

Outstanding!! Birch Croft is truly exceptional. We enjoyed all the space inside and out -including two kitchens, a huge game room, quiet nooks to sit and read from the extensive library, a large front porch, spacious bedrooms, a fire pit and of course the absolutely gorgeous 83 acres that surrounded us. We saw three deer and a fox, and took a walk on the trail. Nate was the perfect host-responsive, helpful and courteous-and we appreciated all that he and Olivia have done to make this place so special. Loved the historic vibe, the art and decor, and the very well stocked kitchen (we made dinner for 13 and had everything we needed from silverware to gadgets). DO NOT HESITATE to book here-this is a place to make memories for sure and we look forward to returning again soon.

This was our second time staying at Lauren's beautiful home, and it certainly won’t be our last! The location is absolutely perfect—right on the mountain, making it incredibly convenient! The condo itself is beautifully appointed and stocked with everything you could possibly need for a comfortable stay. One of our favorite features was the wood-burning fireplace, which added a wonderful touch to our evenings after a long day on the slopes. Lauren is a gracious host, always attentive and ready to help with anything we needed. We recommend her place to all our family and friends and look forward to returning next year for more unforgettable memories! Thank you, Lauren, for another fantastic stay!

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

This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!

⭐️⭐️⭐️⭐️⭐️ 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!

Great place to stay if you are in Rutland. The balcony is a great place to relax and the place is amazingly clean and modern. Would definitely stay again

Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.

Great place. I’d definitely stay there again. No complaints about the unit or location. —Fun mountain We got lucky with a powder day! If the beginner slope had been open it would’ve been “Ski in -Ski out” but it wasn’t, so we had a hike to get back to the place. —A skier suggested that I duck under the rope, but I wasn’t familiar with the mountain so I wasn’t comfortable doing that. -It should be mentioned since his unit is @ the Top of the slope and you have to hike it with your gear. I was fine, but it might not be ok for everyone. I guess sometimes you have to break the rules!!🤷🏻‍♀️ I’d recommend Tony’s place!