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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Chester

Interior
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.6 out of 10, Exceptional, (4)
"The Warwick Inn is an amazing stay for anyone trying to escape for a few days. The rooms were amazing, spacious, and comfortable. Gabriela was amazing at setting up our check-in and was always available for any questions we had. Highly recommend. "
United States
Nicolas
The price is AED 311
AED 551 total
includes taxes & fees
27 Oct - 28 Oct
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed
3BR West Point Retreat-3min to Back Gate+ King Bed
9.0 out of 10, Wonderful, (2)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
The price is AED 573
AED 1,812 total
includes taxes & fees
28 Oct - 29 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
10.0 out of 10, Exceptional, (3)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is AED 536
AED 1,387 total
includes taxes & fees
2 Nov - 3 Nov
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Interior
Lovely 3BR Home with parking-Walk to WP Gate!
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (7)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
United States
Molly s.
The price is AED 679
AED 1,121 total
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
Property grounds
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, (41)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
United States
Louise S.
The price is AED 526
AED 1,116 total
includes taxes & fees
26 Oct - 27 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AED 613
AED 1,774 total
includes taxes & fees
29 Oct - 30 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (56)
"Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location "
United States
Mamie G.
The price is AED 658
AED 1,448 total
includes taxes & fees
27 Oct - 28 Oct
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very Good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
The price is AED 683
AED 1,136 total
includes taxes & fees
17 Nov - 18 Nov
Fabulous 3bdrm Home w/parking!
Interior
Charming bungalow in lovely Middletown NY
Charming bungalow in lovely Middletown NY
The price is AED 496
AED 720 total
includes taxes & fees
25 Oct - 26 Oct
Charming bungalow in lovely Middletown NY
Exterior
West Point Family Retreat, 5 min walk to Thayer!
West Point Family Retreat, 5 min walk to Thayer!
2.0 star property
9.8 out of 10, Exceptional, (6)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
United States
Randall T.
The price is AED 1,653
AED 3,037 total
includes taxes & fees
27 Oct - 28 Oct
West Point Family Retreat, 5 min walk to Thayer!
Interior
Lux Lake Neepaulin Front Home
Lux Lake Neepaulin Front Home
8.0 out of 10, Very Good, (2)
"Nice place to stay. "
United States
Bob
The price is AED 621
AED 1,102 total
includes taxes & fees
27 Oct - 28 Oct
Lux Lake Neepaulin Front Home
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.8 out of 10, Exceptional, (41)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is AED 951
AED 1,213 total
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
9.8 out of 10, Exceptional, (58)
"We had a wonderful stay! The house is in a beautiful location, everything was well appointed, instructions were easy to follow and the house itself was perfect. "
United States
Katie
The price is AED 918
AED 1,837 total
includes taxes & fees
23 Nov - 24 Nov
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Interior
Contemporary Cozy Cottage
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (28)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AED 826
AED 1,554 total
includes taxes & fees
29 Oct - 30 Oct
Contemporary Cozy Cottage
Fridge, microwave, oven, stovetop
Private Mountain Creek Getaway!
Private Mountain Creek Getaway!
8.4 out of 10, Very Good, (5)
"The property is very comfortable and clean. It is convenient to the ski area, Warwick, New York's apple orchards and fun main street shopping, Penning's Cidery & Orchard. The driveway is steep, if you have multiple cars, parking across the street (if allowed) may be preferred."
United States
Patricia S.
The price is AED 752
AED 1,663 total
includes taxes & fees
27 Oct - 28 Oct
Private Mountain Creek Getaway!
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres
Stylish & Peaceful Getaway on 3 Private Acres
2.0 star property
9.0 out of 10, Wonderful, (12)
"The owner was extremely responsive and the home was very clean."
United States
Christine C.
The price is AED 1,058
AED 1,609 total
includes taxes & fees
26 Oct - 27 Oct
Stylish & Peaceful Getaway on 3 Private Acres
Dining tables
Chestnut on Willow Lake
Chestnut on Willow Lake
9.4 out of 10, Exceptional, (3)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is AED 1,469
AED 2,149 total
includes taxes & fees
27 Oct - 28 Oct
Chestnut on Willow Lake
Pool
⛷Modern 3bd2bth, walk to SPA & dining
⛷Modern 3bd2bth, walk to SPA & dining
9.8 out of 10, Exceptional, (14)
"Great time and condo was perfect for socializing!"
United States
Sarah E.
The price is AED 885
AED 1,481 total
includes taxes & fees
5 Nov - 6 Nov
⛷Modern 3bd2bth, walk to SPA & dining
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AED 1,587
AED 2,521 total
includes taxes & fees
26 Oct - 27 Oct
Large,Cozy,Bright Apartment, Business Themed.
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"We had two minor issues. The TV was set to the wrong mode making viewing impossible and the lighting was poor in the corner near the coffee table. The staff handled these issues quickly and efficiently by adjusting the back of the TV and by providing a standing floor lamp. We appreciated the service and the comfort of the rooms."
Betty Jean 2-night trip
Posted 7 hours ago
Quality Inn & Suites Fishkill South near I-84