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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Chester cottages

TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥31,936
￥39,392 total
includes taxes & fees
Mar 4 - Mar 5
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

Cottage in Jamaica

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
10.0 out of 10, Exceptional, (3 reviews)
"Nice and cozy, just like the listing shows. Great host. "
United States
Kytalia B.
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Exterior

Cottage in Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
10.0 out of 10, Exceptional, (1 review)
"House was perfect! Well appointed with everything you need. Beds very comfortable and very clean. Host was very responsive and was there if you needed anything. Will definitely stay again. "
United States
Stephen S.
The price is ￥35,111
￥94,728 total
includes taxes & fees
Mar 4 - Mar 5
Terrific 3-bedroom cottage with AC in charming Cavendish
House (5 Bedrooms) | Interior

Cottage in Ludlow

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
The price is ￥171,811
￥267,212 total
includes taxes & fees
Mar 4 - Mar 5
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

On The River Inn

On The River Inn

10/10 Excellent
"Friendly and helpful staff "
susan 2-night trip
Posted 2 days ago
On The River Inn

Find out more about Chester

Chester Cottages information

Number of reviews
12
Accommodation
162 Cottages
Lowest Price
￥39,392
Highest Price
￥267,212

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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