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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Vacation Homes in Chester

Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.2 out of 10, Wonderful, (7)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is AED 304
AED 544 total
includes taxes & fees
10 Dec - 11 Dec
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AED 602
AED 1,763 total
includes taxes & fees
21 Dec - 22 Dec
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (5)
The price is AED 584
AED 1,586 total
includes taxes & fees
21 Dec - 22 Dec
House on the Babbling Brook- Quiet 2BR + 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
Warwick
10.0 out of 10, Exceptional, (5)
The price is AED 518
AED 1,363 total
includes taxes & fees
17 Dec - 18 Dec
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Goshen
10.0 out of 10, Exceptional, (58)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is AED 909
AED 1,736 total
includes taxes & fees
4 Jan - 5 January 2026
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
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

Wurtsboro
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Interior
Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls
10.0 out of 10, Exceptional, (7)
"Convenient location. Nice to have 3 queen beds. One parking space is in a lot, but street for any additional. Plenty of availability though. Excellent washer and dryer, dishwasher. Internet worked well. "
United States
Matt D.
The price is AED 690
AED 1,269 total
includes taxes & fees
5 Jan - 6 January 2026
Lovely 3BR Home with parking-Walk to WP Gate!
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

Fishkill
9.6 out of 10, Exceptional, (49)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
The price is AED 909
AED 1,161 total
includes taxes & fees
10 Dec - 11 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!

Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 667
AED 1,208 total
includes taxes & fees
5 Jan - 6 January 2026
Fabulous 3bdrm Home w/parking!
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

Vernon Township
9.4 out of 10, Exceptional, (44)
"Beautiful area"
United States
Joseph D.
The price is AED 526
AED 1,116 total
includes taxes & fees
12 Dec - 13 Dec
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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!

wallkill
9.8 out of 10, Exceptional, (57)
"Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location "
United States
Mamie G.
The price is AED 654
AED 1,445 total
includes taxes & fees
10 Dec - 11 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Interior
Lux Lake Neepaulin Front Home

Lux Lake Neepaulin Front Home

Wantage
7.4 out of 10, Good, (3)
"Nice place to stay. "
United States
Bob
The price is AED 364
AED 760 total
includes taxes & fees
10 Dec - 11 Dec
Lux Lake Neepaulin Front Home
Outdoor spa tub
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Greenwood Lake
10.0 out of 10, Exceptional, (29)
"We loved the house. It was a perfect and much needed short getaway for my husband and I. We brought our little dog Lenny and he loved it too! "
United States
Chelsea D.
The price is AED 578
AED 1,672 total
includes taxes & fees
10 Dec - 11 Dec
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Smart TV, video games, DVD player, foosball
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Pine Bush
9.4 out of 10, Exceptional, (43)
"Such a beautiful home and peaceful farm setting! We especially loved the game room and spacious living areas — perfect for relaxing and spending quality time together as a family. Good location as well! "
United States
Shachi S.
The price is AED 1,247
AED 2,421 total
includes taxes & fees
12 Dec - 13 Dec
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AED 1,322
AED 1,761 total
includes taxes & fees
10 Dec - 11 Dec
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

2.0 star property
Monroe
The price is AED 476
AED 1,519 total
includes taxes & fees
10 Dec - 11 Dec
Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle
Interior
Contemporary Cozy Cottage

Contemporary Cozy Cottage

Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AED 826
AED 1,542 total
includes taxes & fees
10 Dec - 11 Dec
Contemporary Cozy Cottage
Fridge, microwave, oven, stovetop
Private Mountain Creek Getaway!

Private Mountain Creek Getaway!

Vernon Township
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 677
AED 1,514 total
includes taxes & fees
18 Dec - 19 Dec
Private Mountain Creek Getaway!
Outdoor dining
Stylish & Peaceful Getaway on 3 Private Acres

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
Goshen
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
The price is AED 1,058
AED 1,609 total
includes taxes & fees
10 Dec - 11 Dec
Stylish & Peaceful Getaway on 3 Private Acres
Interior
Charming bungalow in lovely Middletown NY

Charming bungalow in lovely Middletown NY

Middletown
The price is AED 496
AED 716 total
includes taxes & fees
10 Dec - 11 Dec
Charming bungalow in lovely Middletown NY
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

10/10 Excellent
"Clean room, helpful staff, great breakfast. Will stay with Hampton Inn and Suites again."
Lisa 1-night trip
Posted 22 hours ago
Hampton Inn & Suites Mahwah