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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Chester cottages

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Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$281 nightly
The price is $293
May 25 - May 26
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds

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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$280 nightly
The price is $331
May 18 - May 19
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$453 nightly
The price is $499
May 18 - May 19
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$395 nightly
The price is $447
May 18 - May 19
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Exterior

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$318 nightly
The price is $359
May 18 - May 19
Total with taxes and fees
Hello Small Stone
Property grounds

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
10.0 out of 10, Exceptional, (1 review)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
$203 nightly
The price is $228
May 18 - May 19
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Outdoor dining

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

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
8.8 out of 10, Excellent, (3 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
May 18 - May 19
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Outdoor pool, a heated pool

Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
$301 nightly
The price is $337
May 19 - May 20
Total with taxes and fees
Private Pool House - Pool · Jacuzzi · Fireplace
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
$505 nightly
The price is $622
Jun 2 - Jun 3
Total with taxes and fees
Updated Home w/ Patio Half Mile to West Point
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
$639 nightly
The price is $723
May 18 - May 19
Total with taxes and fees
Family Home Close to Warwick, 5 Mi to Lake!
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

Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Breakfast is no longer a grab ‘n’ go but a hearty one!! Wonderful! "
Diane 1-night trip
Posted 3 hours ago
Inn on the Hudson

Find out more about Chester

Chester Cottages information

Number of reviews
182
Accommodation
79 Cottages
Lowest Price
$228
Highest Price
$723

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between $228 and $723 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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