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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Chester cottages

Cottage (2 Bedrooms) | Interior

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, (3 reviews)
"fantastic accommodations"
United States
David
The price is CA $256
CA $720 total
includes taxes & fees
Jul 2 - Jul 3
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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, (138 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is CA $277
CA $466 total
includes taxes & fees
Jun 23 - Jun 24
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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
9.0 out of 10, Wonderful, (2 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is CA $210
CA $321 total
includes taxes & fees
Jun 20 - Jun 21
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Smart TV

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.
The price is CA $208
CA $414 total
includes taxes & fees
Jun 17 - Jun 18
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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.
The price is CA $199
CA $554 total
includes taxes & fees
Jun 17 - Jun 18
Hello Small Stone
Property grounds

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (7 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
The price is CA $229
CA $726 total
includes taxes & fees
Jul 2 - Jul 3
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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.
The price is CA $315
CA $674 total
includes taxes & fees
Jun 23 - Jun 24
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is CA $343
CA $625 total
includes taxes & fees
Jun 17 - Jun 18
Hike & Fish: Outdoor Retreat Near Trails
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
Family Home Close to Warwick, 5 Mi to Lake!
House (3 Bedrooms) | Interior

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
Bright Cornwall-on-hudson Vacation Rental!
House (6 Bedrooms) | Interior

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
3.0 star property
Vernon
The price is CA $2,049
CA $4,152 total
includes taxes & fees
Jun 17 - Jun 18
Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"Property was located near many retailers and eateries, hotel was clean, it was under renovations, but other than seeing workers moving materials you would not know it. I can't say for sure, but I believe our room was one of the rooms which had been renovated based on the condition of the furnishings. Kitchen was very nice and is a plus for anyone with an extended stay."
Larry 1-night trip
Posted 11 hours ago
Sonesta Simply Suites Nanuet

Find out more about Chester

Chester Cottages information

Number of reviews
169
Accommodation
80 Cottages
Lowest Price
CA $321
Highest Price
CA $4,152

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between CA $321 and CA $4,152 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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