Holiday Homes in Chester

"Very clean and nice apartment in a pleasant little city."

"Beautiful place, we stayed here after our Six Flags birthday trip and the boys loved the pool and hot tub and the whole atmosphere! 10/10!!!"

"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...

"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."

"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...

"Top notch!! Will definitely be back. Thanks!!"

"Absolutely loved it. Perfect getaway when the city is too noisy. Awesome location in the woods surrounded by nothing but forest. If you plan on staying outside in the hot tub, maybe get one of those bug repellent tiki torches however i got no other complaints. Maybe a tv in the adult bedroom? Anyway good kitchen good bathroom good living room good bedroom for adults good room for children. If youre looking to get away, there isnt anything wrong in picking this place if you desire a forest get...

"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"

"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"

"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"

"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

"Very nice, well stocked and away from the hustle and bustle of city life. We had a great time."

"It was a nice house in a quiet neighborhood, the amenities were up to date and very comfortable place to spend our time."

"My brother and I came to honor our late father, our family used to own property on Laurel lake so it was especially meaningful to us to have access to it for kayaking. The house has central ac which is harder to find, it's got plenty of bedrooms, two of which are on the first floor."

"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."

"Great property. Easy check in and communication with the owner."

"My BF and I really enjoyed the Hawley Home. The location was stunning and quiet. The owner was very kind and responsive when I reached out with questions before we started out on our drive to the location. There was a welcome book with all of the information on the home and it included information about the local attractions. The property is clean, the bed is comfortable and the views are breathtaking. There is no cell service ( not that is a bad thing with as much as we work) but the home has...

"We loved our long weekend here—so comfortable and clean and private. Just perfect for two!"

"Stayed here for my child’s graduation weekend. Enough room for everyone and great location. Loved the nearby walking trail!"