Holiday Homes in Chester

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Check prices for these dates

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

Our top choices for Chester holiday 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 AU$215
includes taxes & fees
31 Mar - 1 Apr
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 AU$458
includes taxes & fees
25 Mar - 26 Mar
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 AU$502
includes taxes & fees
23 Mar - 24 Mar
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 AU$708
includes taxes & fees
6 Apr - 7 Apr
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 AU$468
includes taxes & fees
23 Mar - 24 Mar
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 AU$622
includes taxes & fees
24 Mar - 25 Mar
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 AU$677
includes taxes & fees
24 Mar - 25 Mar
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 AU$442
includes taxes & fees
8 Apr - 9 Apr
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 AU$622
includes taxes & fees
23 Mar - 24 Mar
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 AU$266
includes taxes & fees
22 Mar - 23 Mar
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 AU$596
includes taxes & fees
26 Mar - 27 Mar
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 AU$588
includes taxes & fees
1 Apr - 2 Apr
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 AU$426
includes taxes & fees
27 Mar - 28 Mar
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 AU$554
includes taxes & fees
20 Mar - 21 Mar
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 AU$520
includes taxes & fees
24 Mar - 25 Mar
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 AU$988
includes taxes & fees
30 Mar - 31 Mar
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 AU$448
includes taxes & fees
7 Apr - 8 Apr
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 AU$337
includes taxes & fees
26 Mar - 27 Mar
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 AU$532
includes taxes & fees
1 Apr - 2 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.
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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 8 hours ago
Hampton Inn Nanuet

Find out more about Chester

Chester Holiday Homes information

Number of reviews
267
Accommodation
301 Holiday Homes
Lowest Price
AU$215
Highest Price
AU$988