Search Chester Cottage Rentals from CA $358

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

In two weeks

In one month

In two months

Browse Select Chester Cottages

Relax by the campfire in a serene wooded setting, surrounded by Adirondack chairs and a rustic picnic table.

"Great place just need the fire place to be fixed asap, especially for the winter time"

Cozy space with a high ceiling, round table, and four chairs, surrounded by large windows and a decorative wreath.

"Very cozy cabin for a weekend getaway. Multiple fireplaces with plenty of firewood available. Great place to curl up with a book or lots of shopping / restaurants in the area. "

Set amidst lush greenery, this traditional building offers a serene and retreat with a gabled roof and symmetrical facade.

"Location was great!!"

Relax on the lakeside dock, surrounded by serene woods and a tranquil atmosphere.

"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."

Relax in the cottage's outdoor seating area, featuring a wicker chair, cushioned bench, and small table.

"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."

Escape to a secluded cabin surrounded by tall trees, featuring a cozy porch and outdoor speakers for a peaceful retreat.

"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."

Enjoy meals in the well-appointed kitchen and dining area, featuring a stainless steel stove, microwave, and wooden table for four.

"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"

Enjoy cooking in this well-equipped kitchen with a stainless steel sink, toaster, microwave, and stove with digital controls.

"very good cozy location. enjoyed the privacy during our stay."

Enjoy cooking in this well-equipped kitchen with an oven, range hood, and stainless steel sink.

"The Carriage House is lovely and surroundings beautiful. We had a very relaxing experience. Lizzie was a perfect host."

Set amidst lush greenery, this charming house features a gabled roof and a welcoming porch.

"This was a great location… close to town but also close to skiing, hiking and skating."

"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."

"Would definitely recommend! House had an everything we would need. So comfy and cozy! "

Relax in this inviting living room with a checkered armchair, sofa, and dining table.

"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "

CA $443 total

includes taxes & fees

Aug 7 - Aug 8

Set amidst a serene wooded area, this charming home features a traditional gabled roof and a central chimney.

"Had a great stay at the old school house. Location was perfect for what we needed. Place was super clean and well appointed. Would love to come back again."