Search Chester Cottage Rentals from CA $193

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chester Cottages

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is CA $278
CA $449 total
includes taxes & fees
Aug 6 - Aug 7
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Fridge, microwave, oven, stovetop

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is CA $379
CA $831 total
includes taxes & fees
Sep 3 - Sep 4
Charming Cottage in the Heart of the Shawangunks
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is CA $223
CA $575 total
includes taxes & fees
Aug 6 - Aug 7
Hello Small Stone
Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is CA $252
CA $446 total
includes taxes & fees
Aug 6 - Aug 7
Hike & Fish: Outdoor Retreat Near Trails
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (102)
"For the dogs: our dogs enjoyed the big fenced-in backyard. There's also a HUGE fenced-in dog run a few minutes drive away. For the humans: My wife and I enjoyed the gaming options (Xbox, Playstation, and an arcade machine). There's a nice little town a few minutes drive away, with a supermarket, CVS, and decent coffee and food options."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Fridge, microwave, stovetop, dishwasher

Hudson Valley Retreat w/ Pool Near Greenwood Lake

10.0 out of 10, Exceptional, (6)
"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!"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Smart TV, fireplace

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

9.6 out of 10, Exceptional, (13)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Outdoor dining

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

The price is CA $193
CA $294 total
includes taxes & fees
Aug 13 - Aug 14
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Luxe Family Home on Orange Lake w/ Private Dock!
House (3 Bedrooms) | Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excelent House 👏👌👌"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cozy Haven: A Romantic Retreat in our Tiny House!
TV, fireplace

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is CA $207
CA $407 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Haven: A Romantic Retreat in our Tiny House!
Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Living area

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Outdoor dining

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

2.0 star property
8.0 out of 10, Very good, (2)
"Nice"
The price is CA $310
CA $665 total
includes taxes & fees
Aug 11 - Aug 12
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Charming Gardiner Home w/ Yard & Sunroom
House (3 Bedrooms) | Interior

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom
Family Home Close to Warwick, 5 Mi to Lake!
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

3.0 star property
Family Home Close to Warwick, 5 Mi to Lake!
Bright Cornwall-on-hudson Vacation Rental!
House (3 Bedrooms) | Interior

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
All-season Vernon Township Lake House Retreat!
Interior

All-season Vernon Township Lake House Retreat!

3.0 star property
All-season Vernon Township Lake House Retreat!
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Fridge, microwave, oven, stovetop

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (151)
"The property was very clean and the view atmosphere was amazing"
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Historic 1800s Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (29)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Children's area

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (10)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
The price is CA $205
CA $403 total
includes taxes & fees
Aug 11 - Aug 12
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"We had a great stay here. The manager was the best (Corlina? Corvina?) Everything was clean and the room was super comfortable. And the breakfast was off the charts! Waffles, eggs, delicious pastries, French toast…. Best breakfast I’ve had at a hotel that was included with the room! The only negative was the pool area was overcrowded, loud and full of kids who couldn’t have been potty trained but weren’t in swim diapers…"
Oveta 1-night trip
Posted 12 hours ago
Sleep Inn & Suites Middletown - Goshen