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Search Chester Cottage Rentals from CA $582

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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.
The price is CA $312
CA $841 total
includes taxes & fees
Aug 18 - Aug 19
Terrific 3-bedroom cottage with AC in charming Cavendish
House (2 Bedrooms) | Interior

2. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is CA $359
CA $582 total
includes taxes & fees
Aug 19 - Aug 20
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
TV, books

3. 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
The price is CA $408
CA $504 total
includes taxes & fees
Aug 19 - Aug 20
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is CA $551
CA $709 total
includes taxes & fees
Sep 14 - Sep 15
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
House (5 Bedrooms) | Interior

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is CA $1,651
CA $2,656 total
includes taxes & fees
Aug 18 - Aug 19
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
House (4 Bedrooms) | Interior

6. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is CA $527
CA $907 total
includes taxes & fees
Aug 18 - Aug 19
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

Claremont Motor Lodge

Claremont Motor Lodge

10/10 Excellent
"I was pleasantly surprised by the Claremont Motor Lodge. It is clean, safe, and quiet, and nicely set back from the main road. Would definitely stay again."
Louise 1-night trip
Posted 2 hours ago
Claremont Motor Lodge

Find out more about Chester

Chester Cottages information

Number of reviews
Accommodation
177 Cottages
Lowest Price
CA $582
Highest Price
CA $2,656

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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