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Our top choices for Chester cottages

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
Jul 1 - Jul 2
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish

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)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
$266 nightly
The price is $289
Jul 1 - Jul 2
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$406 nightly
The price is $447
Jul 1 - Jul 2
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

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
Jul 1 - Jul 2
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

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
Jul 1 - Jul 2
Total with taxes and fees
3 Mi to Mount Snow: Spacious West Dover Home

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,679 nightly
The price is $1,847
Jul 1 - Jul 2
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

Find out more about Chester

Chester Cottages information

Number of reviews
11
Accommodation
177 Cottages
Lowest Price
$289
Highest Price
$1,847

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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