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Search Chester Cottage Rentals from CA $424

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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
The price is CA $211
CA $424 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $276
CA $788 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is CA $587
CA $755 total
includes taxes & fees
Oct 20 - Oct 21
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
The price is CA $208
CA $573 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is CA $1,950
CA $3,052 total
includes taxes & fees
Oct 2 - Oct 3
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
The price is CA $539
CA $1,109 total
includes taxes & fees
Oct 12 - Oct 13
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

On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 1 hour ago
On The River Inn

Find out more about Chester

Chester Cottages information

Number of reviews
3
Accommodation
176 Cottages
Lowest Price
CA $424
Highest Price
CA $3,052

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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