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Search Chester Cottages

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chester cottages

A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

1. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
$461 nightly
The price is $545
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$283 nightly
The price is $295
Nov 1 - Nov 2
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

3. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
$457 nightly
The price is $517
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A rustic cabin with a stone exterior, wooden deck, and a small porch.

4. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$328 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
Hello Small Stone
A house with a view of a bridge and mountains.

5. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (149 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 28 - Oct 29
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

6. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
$192 nightly
The price is $216
Oct 27 - Oct 28
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
An outdoor dining area with tables and chairs, surrounded by greenery and a view of the landscape.

7. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.2 out of 10, Wonderful, (5 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Oct 27 - Oct 28
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

8. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$685 nightly
The price is $756
Nov 21 - Nov 22
Total with taxes and fees
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A wooden deck with a barbecue grill and a trash can.

9. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Oct 27 - Oct 28
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

10. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
$591 nightly
The price is $698
Nov 22 - Nov 23
Total with taxes and fees
Bright Cornwall-on-hudson Vacation Rental!
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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Great experience and location! Loved my stay."
Clay 1-night trip
Posted less than an hour ago
The Thayer Hotel at West Point

Find out more about Chester

Chester Cottages information

Number of reviews
177
Accommodation
82 Cottages
Lowest Price
$216
Highest Price
$756

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between $216 and $756 per night. Whatever your budget, you're sure to find an ideal place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
Booking a cottage in Chester is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We've have them as well!
How can I find cheap cottages in Chester?
With Expedia's useful filter tool, scoring cheap cottages in Chester is a snap. To find properties that'll make your hip pocket happy, refine your search by amenities, star rating and budget.
What is there to do in Chester near my cottage?
Once you've settled into your hotel, head out and discover the wonderful things Chester has on offer. Castle Fun Center is a popular attraction to add to your must-see list.

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