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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chester cottages

A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

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

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
$271 nightly
The price is $298
Oct 4 - Oct 5
Total with taxes and fees
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

2. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
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.
$508 nightly
The price is $569
Nov 1 - Nov 2
Total with taxes and fees
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Exterior

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$473 nightly
The price is $534
Oct 20 - Oct 21
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
A house with a deck, surrounded by trees and a grassy slope.

4. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A green wooden house with a sloped roof and a front porch.

5. 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
Oct 2 - Oct 3
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
A wooden deck leading to a house with a view of a road and greenery.

6. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
$710 nightly
The price is $781
Oct 4 - Oct 5
Total with taxes and fees
Spacious Vermont Farmhouse 3 Mi to Mount Snow
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

Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Modern, clean, easy access and parking and good location. Touchless check in was easy and efficient."
Joseph 1-night trip
Posted 9 hours ago
Aspen At Manchester

Find out more about Chester

Chester Cottages information

Number of reviews
3
Accommodation
176 Cottages
Lowest Price
$298
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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