Holiday Homes in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Chester holiday homes

Interior

Holiday Home in Warwick

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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 NZ$258
includes taxes & fees
31 Mar - 1 Apr
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
TV

Holiday Home in Highland Falls

Luxury House Near West Point
The price is NZ$541
includes taxes & fees
23 Mar - 24 Mar
Luxury House Near West Point
Terrace/patio

Holiday Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$602
includes taxes & fees
23 Mar - 24 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
Outdoor spa tub

Holiday Home in Goshen

Country House w/Hot Tub, Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (61 reviews)
"Very good host "
United States
Binyomin
The price is NZ$862
includes taxes & fees
22 Mar - 23 Mar
Country House w/Hot Tub, Deck, Grill & Fire Pit
Interior

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
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 NZ$546
includes taxes & fees
23 Mar - 24 Mar
Lovely 3BR Home with parking-Walk to WP Gate!
3 bedrooms, desk, iron/ironing board, free WiFi

Holiday Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
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 NZ$751
includes taxes & fees
23 Mar - 24 Mar
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Outdoor spa tub

Holiday Home in Greenwood Lake

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
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 NZ$846
includes taxes & fees
23 Mar - 24 Mar
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Exterior detail

Holiday Home in Highland Falls

Fabulous 3bdrm Home w/parking!
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 NZ$541
includes taxes & fees
8 Apr - 9 Apr
Fabulous 3bdrm Home w/parking!
Property grounds

Holiday Home in Highland Falls

3BR West Point Retreat-3min to Back Gate+ King Bed
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 NZ$749
includes taxes & fees
23 Mar - 24 Mar
3BR West Point Retreat-3min to Back Gate+ King Bed
Interior

Holiday Home in Wantage

Lux Lake Neepaulin Frontage & Panoramic Views Home
7.8 out of 10, Good, (7 reviews)
"Nice place to stay. "
United States
Bob
The price is NZ$318
includes taxes & fees
23 Mar - 24 Mar
Lux Lake Neepaulin Frontage & Panoramic Views Home
Interior

Holiday Home in Vernon Township

Private Mountain Creek Getaway!
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 NZ$719
includes taxes & fees
22 Mar - 23 Mar
Private Mountain Creek Getaway!
Fridge, microwave, oven, stovetop

Holiday Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is NZ$723
includes taxes & fees
1 Apr - 2 Apr
Contemporary Cozy Cottage
Smart TV, fireplace

Holiday Home in Vernon Township

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, (54 reviews)
"Great place to stay!"
United States
Michele B.
The price is NZ$521
includes taxes & fees
27 Mar - 28 Mar
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds

Holiday Home in Cornwall

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
10.0 out of 10, Exceptional, (7 reviews)
The price is NZ$674
includes taxes & fees
20 Mar - 21 Mar
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Property grounds

Holiday Home in wallkill

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
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 NZ$613
includes taxes & fees
24 Mar - 25 Mar
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Interior

Holiday Home in Greenwood Lake

Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
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 NZ$1,196
includes taxes & fees
29 Mar - 30 Mar
Entire Lakeview House ~ Hot Tub ~ Firepit ~ Stunning View ~ Spacious Deck
Fridge, microwave, oven, stovetop

Holiday Home in Highland Falls

Luxury Townhouse Near West Point
The price is NZ$541
includes taxes & fees
22 Mar - 23 Mar
Luxury Townhouse Near West Point
Exterior

Holiday Home in Highland Falls

Luxury home near West Point
10.0 out of 10, Exceptional, (1 review)
The price is NZ$395
includes taxes & fees
31 Mar - 1 Apr
Luxury home near West Point
Pool

Holiday Home in Vernon Township

⛷Modern 3bd2bth, walk to SPA & dining
9.8 out of 10, Exceptional, (19 reviews)
"Great location, very relaxing stay. "
United States
Dan P.
The price is NZ$650
includes taxes & fees
31 Mar - 1 Apr
⛷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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 5 hours ago
Hampton Inn Nanuet

Find out more about Chester

Chester Holiday Homes information

Number of reviews
267
Accommodation
326 Holiday Homes
Lowest Price
NZ$258
Highest Price
NZ$1,196