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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chester cottages

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

1. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is NZ$891
includes taxes & fees
9 Nov - 10 Nov
Renovated Vermont Retreat with mountain views near Okemo & Killington for 6
A green wooden house with a sloped roof and a front porch.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is NZ$3,844
includes taxes & fees
17 Nov - 18 Nov
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Terrace/patio

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is NZ$1,265
includes taxes & fees
8 Nov - 9 Nov
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
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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Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top reviews in Chester

A white building with a stone chimney, multiple windows, and a porch with potted plants.
The Manchester View

The Manchester View

The Manchester View
Manchester Center

10/10 Excellent

.
Australia
Sharon
Reviewed October 15, 2023
The Manchester View

Frequently Asked Questions

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.