Photo by Elizabeth Massa Peroulakis

Search Vacation Homes in Chester

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Compare 213 Vacation Homes in Chester with updated reviews, rates, and availability.

"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "

AED 821 total

includes taxes & fees

30 Dec - 31 Dec

Main Level LR sliding doors to Front Deck lake view, open to the dining room.

"We had a lovely stay! The space was perfect for our group of 4 moms looking for a peaceful getaway. The host was very responsive. Only note for those visiting, rideshares (Uber and otherwise) are few and far between. Schedule ahead! We'd definitely stay again :)"

"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "

The Valley is known for our picturesque red tobacco barns and expansive cornfields.

"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "

Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...

"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"

Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...

"As advertised "

"Very nice place, clean, great communication. "

"Convenient location, comfortable."

AED 943 total

includes taxes & fees

22 Jan - 23 January 2025

View of house as seen from road near the brook

"A cozy spot to watch the snow come down!"

Bike ride on the Norwottuck Rail Trail( entrance to trail 2-minutes from the house) to the CT River- Bring your bikes and enjoy!

"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "

"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."

AED 1,402 total

includes taxes & fees

31 Dec - 1 January 2025

"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "

View from deck looking over our dock on a still day in last days of October.

"Highly recommend this house. Wonderful location, plenty of beds for a group. Great communication with the host."

"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"