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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Chester cottages

Exterior
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
Jamaica
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. "
United States
Kyle M.
$221 nightly
The price is $250
Jan 15 - Jan 16
Total with taxes and fees
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
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

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.
$270 nightly
The price is $293
Jan 25 - Jan 26
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior
Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
$543 nightly
The price is $608
Jan 12 - Jan 13
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
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

The Manchester View

The Manchester View

10/10 Excellent
"Yes"
David 1-night trip
Posted 2 days ago
The Manchester View

Find out more about Chester

Chester Cottages information

Number of reviews
10
Accommodation
162 Cottages
Lowest Price
$250
Highest Price
$608

Frequently asked questions

Why book your cottage in Chester with Expedia?
We think that traveling should be a walk in the park, so if you're on the lookout for cottages in Chester at a competitive price, Expedia has you covered. Stick to the budget and choose a cheap option far from the hustle and bustle, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Chester?
Expedia can help you look for cheap cottages in Chester. To reserve a superb stay in a few quick clicks, try out our handy filter tool to refine your search by amenities, star rating and budget.
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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