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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Chester vacation homes

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
9.0 out of 10, Wonderful, (11 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is ￥13,231
￥23,646 total
includes taxes & fees
Mar 30 - Mar 31
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ￥31,635
￥51,433 total
includes taxes & fees
Mar 23 - Mar 24
Luxury House Near West Point
Terrace/patio

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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥15,979
￥57,266 total
includes taxes & fees
Mar 24 - Mar 25
House on the Babbling Brook- Quiet 2BR + King Bed!
Outdoor spa tub

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (61 reviews)
"Very good host "
United States
Binyomin
The price is ￥41,094
￥77,924 total
includes taxes & fees
Mar 22 - Mar 23
Country House w/Hot Tub, Deck, Grill & Fire Pit
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 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is ￥26,576
￥52,158 total
includes taxes & fees
Mar 23 - Mar 24
Lovely 3BR Home with parking-Walk to WP Gate!
3 bedrooms, desk, iron/ironing board, free WiFi

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is ￥20,293
￥70,258 total
includes taxes & fees
Mar 24 - Mar 25
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (36 reviews)
"House was great, it had everything we needed and even provided coffee! "
United States
Colleen E.
The price is ￥29,561
￥78,631 total
includes taxes & fees
Mar 23 - Mar 24
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (5 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥26,591
￥49,662 total
includes taxes & fees
Apr 8 - Apr 9
Fabulous 3bdrm Home w/parking!
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is ￥17,577
￥69,416 total
includes taxes & fees
Mar 23 - Mar 24
3BR West Point Retreat-3min to Back Gate+ King Bed
Interior

Lux Lake Neepaulin Frontage & Panoramic Views Home

Lux Lake Neepaulin Frontage & Panoramic Views Home
Wantage
7.8 out of 10, Good, (7 reviews)
"Nice place to stay. "
United States
Bob
The price is ￥20,984
￥29,430 total
includes taxes & fees
Mar 22 - Mar 23
Lux Lake Neepaulin Frontage & Panoramic Views Home
Interior

Private Mountain Creek Getaway!

Private Mountain Creek Getaway!
Vernon Township
8.8 out of 10, Excellent, (6 reviews)
"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 ￥29,293
￥68,064 total
includes taxes & fees
Mar 26 - Mar 27
Private Mountain Creek Getaway!
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,953
￥65,794 total
includes taxes & fees
Apr 1 - Apr 2
Contemporary Cozy Cottage
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, (54 reviews)
"Great place to stay!"
United States
Michele B.
The price is ￥22,749
￥47,361 total
includes taxes & fees
Mar 27 - Mar 28
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (7 reviews)
The price is ￥30,999
￥63,659 total
includes taxes & fees
Mar 20 - Mar 21
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Property grounds

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (57 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is ￥30,045
￥64,096 total
includes taxes & fees
Mar 30 - Mar 31
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Interior

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Greenwood Lake
10.0 out of 10, Exceptional, (7 reviews)
"We had lovely and relaxing stay at this property! The surrounding area is beautiful and the crowd are amazing!"
United States
Susan R.
The price is ￥53,652
￥118,782 total
includes taxes & fees
Mar 23 - Mar 24
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Fridge, microwave, oven, stovetop

Luxury Townhouse Near West Point

Luxury Townhouse Near West Point
Highland Falls
The price is ￥31,635
￥51,433 total
includes taxes & fees
Mar 22 - Mar 23
Luxury Townhouse Near West Point
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (1 review)
The price is ￥31,635
￥36,814 total
includes taxes & fees
Mar 22 - Mar 23
Luxury home near West Point
Pool

⛷Modern 3bd2bth, walk to SPA & dining

⛷Modern 3bd2bth, walk to SPA & dining
Vernon Township
9.8 out of 10, Exceptional, (19 reviews)
"Great location, very relaxing stay. "
United States
Dan P.
The price is ￥35,453
￥59,232 total
includes taxes & fees
Mar 31 - Apr 1
⛷Modern 3bd2bth, walk to SPA & dining
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 Nanuet

Hampton Inn Nanuet

10/10 Excellent
"Room was spacious and clean. Door closing sound was a bit louder near from the elevator. Other than that I love the hotel. "
Sarah 1-night trip
Posted 11 hours ago
Hampton Inn Nanuet

Find out more about Chester

Chester Vacation Homes information

Number of reviews
267
Accommodation
326 Vacation Homes
Lowest Price
￥23,646
Highest Price
￥118,782