Search Cottages in Chester

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

16 Jum. I - 18 Jum. I

In two weeks

23 Jum. I - 25 Jum. I

In one month

6 Jum. II - 8 Jum. II

In two months

4 Raj. - 6 Raj.

Compare 89 Cottages in Chester with updated reviews, rates, and availability.

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

"Great hosts who made our stay enjoyable. Very peaceful location. "

"A short getaway with family. "

"Beautiful home with a great location in the Berkshires. We had a wonderful time!"

"Excellent property: would have liked to stay longer. "

"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."

"We had a great time. The owner Bill was a great host."

"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."

"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "

"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."

"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...

"2nd time here so I give it excellent review."

SAR 1,041 total

includes taxes & fees

2 Jun - 3 Jun

"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "

"Very nice house. Owners very helpful."

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chester

"Very comfortable property in a lovely setting "

SAR 582 total

includes taxes & fees

11 May - 12 May

"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "

SAR 1,085 total

includes taxes & fees

12 May - 13 May

Recent reviews of Chester hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent

"Great location, friendly staff, and clean/comfortable room!"

A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection

Posted 3 days ago

5/5 Excellent

"I had a wonderful stay at The Yankee, Trademark Collection by Wyndham. The room was beautiful and comfortable, making for a very relaxing experience. The staff was incredibly kind, welcoming, and made check-in and check-out effortless. However, during my visit, there was construction happening nearby, which was quite noisy and inconvenient as it was right next to our room. Additionally, the lobby was not accessible at the time, which was a bit disappointing. Despite these minor issues, my overall experience was positive, largely thanks to the excellent staff and comfortable accommodations."

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham

Posted 3 days ago