A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chester cottages

Exterior

1. 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.
$543 nightly
The price is $608
Sep 2 - Sep 3
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
Living area

2. 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
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
$318 nightly
The price is $345
Sep 2 - Sep 3
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
House (5 Bedrooms) | Interior

3. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,955 nightly
The price is $2,151
Sep 2 - Sep 3
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Exterior

4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$440 nightly
The price is $497
Sep 2 - Sep 3
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
House (4 Bedrooms) | Interior

5. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
$594 nightly
The price is $653
Sep 2 - Sep 3
Total with taxes and fees
3 Mi to Mount Snow: Spacious West Dover Home
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great place. Staff are very nice and helpful."
Jonathan 2-night trip
Posted 14 hours ago
Latchis Hotel

Find out more about Chester

Chester Cottages information

Number of reviews
11
Accommodation
176 Cottages
Lowest Price
$345
Highest Price
$2,151

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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