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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chester cottages

House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
$376 nightly
The price is $410
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-site: Cozy Falls Brook Cabin
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$263 nightly
The price is $286
May 26 - May 27
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Nice and cozy, just like the listing shows. Great host. "
United States
Kytalia B.
$181 nightly
The price is $205
May 29 - May 30
Total with taxes and fees
Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
Exterior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$536 nightly
The price is $600
May 26 - May 27
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
House (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
$670 nightly
The price is $737
Jun 4 - Jun 5
Total with taxes and fees
3 Mi to Mount Snow: Spacious West Dover Home
House (5 Bedrooms) | Interior

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,471 nightly
The price is $1,619
May 26 - May 27
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

6/10 Okay
"The hotel is visibly aging and requires both upgrades and basic maintenance. During my stay, multiple room fixtures did not function properly, including the sink and the toilet. Additionally, the breakfast bar was sparse; there were no juices or standard breakfast beverages available, leaving water as the only option. The property management needs to address these infrastructure and service gaps."
Matthew 1-night trip
Posted 1 hour ago
Days Inn by Wyndham Keene NH

Find out more about Chester

Chester Cottages information

Number of reviews
13
Accommodation
168 Cottages
Lowest Price
$205
Highest Price
$1,619

Frequently asked questions

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What is there to do in Chester near my cottage?
Once you've unpacked your suitcases, venture out and discover the incredible things Chester has on offer. DaVallia Art & Accents is a top attraction to add to your must-do list.

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