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  • Upfront pricing

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

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chester cottages

A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

1. 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.
$261 nightly
The price is $273
Nov 12 - Nov 13
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.

2. 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
$428 nightly
The price is $506
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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 $539
Nov 30 - Dec 1
Total with taxes and fees
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A house with a view of a bridge and mountains.

4. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
$257 nightly
The price is $304
Nov 16 - Nov 17
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A rustic cabin with a stone exterior, wooden deck, and a small porch.

5. 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.
$382 nightly
The price is $432
Nov 15 - Nov 16
Total with taxes and fees
Hello Small Stone
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.
$189 nightly
The price is $213
Nov 10 - Nov 11
Total with taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A wooden deck with a white railing, surrounded by a grassy lawn and trees.

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.
$403 nightly
The price is $460
Nov 10 - Nov 11
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

8. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$304 nightly
The price is $344
Nov 10 - Nov 11
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
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

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

8/10 Good
"Under renovations but looks like nearly complete. The place should be real nice when complete but was a little dusty in the common areas and used a temporary breakfast room with basic offerings. Our room however was like new, clean and very comfortable,"
Michael 1-night trip
Posted 9 hours ago
Hampton Inn & Suites Mahwah

Find out more about Chester

Chester Cottages information

Number of reviews
178
Accommodation
82 Cottages
Lowest Price
$213
Highest Price
$698

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between $213 and $698 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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