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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chester holiday homes

Coffee/tea maker, fridge, microwave, oven

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is £343
includes taxes & fees
2 Aug - 3 Aug
Contemporary Cozy Cottage
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"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 £527
includes taxes & fees
20 Jul - 21 Jul
Chestnut on Willow Lake
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is £552
includes taxes & fees
20 Jul - 21 Jul
Red Cottage - Lakeside Property!
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
9.2 out of 10, Wonderful, (70 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is £246
includes taxes & fees
22 Jul - 23 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 £391
includes taxes & fees
20 Jul - 21 Jul
Lovely 3BR Home with parking-Walk to WP Gate!
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is £379
includes taxes & fees
20 Jul - 21 Jul
Fabulous 3bdrm Home w/parking!
Exterior

Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is £420
includes taxes & fees
13 Aug - 14 Aug
Hickory on Willow Lake
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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is £304
includes taxes & fees
21 Jul - 22 Jul
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

Luxury 10BR w/Pool, Hot Tub & Pizza Oven

Luxury 10BR w/Pool, Hot Tub & Pizza Oven
Stony Point
The price is £3,905
includes taxes & fees
12 Aug - 13 Aug
Luxury 10BR w/Pool, Hot Tub & Pizza Oven
Smart TV, offices

River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington
Newburgh
River Views & Hot Tub | Riverview on Washington
House | 7 bedrooms

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is £1,225
includes taxes & fees
21 Jul - 22 Jul
West Point Summer Pool Jacuzzi Events Pets OK
Interior

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
8.8 out of 10, Excellent, (16 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is £405
includes taxes & fees
25 Jul - 26 Jul
Large,Cozy,Bright Apartment, Business Themed.
Interior

Harriman Outdoor Center - Stone Lodge

Harriman Outdoor Center - Stone Lodge
Haverstraw
The price is £725
includes taxes & fees
11 Aug - 12 Aug
Harriman Outdoor Center - Stone Lodge
Outdoor spa tub

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, (10 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is £313
includes taxes & fees
20 Jul - 21 Jul
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Private kitchen

Perfect and Spacious Hudson Valley Escape!

Perfect and Spacious Hudson Valley Escape!
Cornwall
8.0 out of 10, Very good, (2 reviews)
"Great host, very responsive and accommodating. The house was very clean and comfortable."
United States
Joseph S.
The price is £613
includes taxes & fees
19 Jul - 20 Jul
Perfect and Spacious Hudson Valley Escape!
Pool

complete privacy vacation home [private pool]

complete privacy vacation home [private pool]
Newburgh
9.2 out of 10, Wonderful, (15 reviews)
"oh my god the best place it feels like home"
United States
Phelicia G.
The price is £882
includes taxes & fees
22 Jul - 23 Jul
complete privacy vacation home [private pool]
Coffee/tea maker, fridge, microwave, oven

Marvelous 6-bedroom house with AC in Monroe

Marvelous 6-bedroom house with AC in Monroe
Monroe
The price is £2,618
includes taxes & fees
10 Aug - 11 Aug
Marvelous 6-bedroom house with AC in Monroe
Coffee/tea maker, fridge, microwave, oven

3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"My wife and I traveled to West Point this weekend with my brother-in-law and sister-in-law to see our son compete in Army Navy track meet. I the house was perfect for us and an easy drive to West Point. House was clean, and well organized. We would stay again."
United States
Ronnie S.
The price is £399
includes taxes & fees
22 Jul - 23 Jul
3BR Hudson Valley home perfect for families!
4 bedrooms, desk, iron/ironing board, WiFi

Lakefront Paradise Pool + Paddle Boats Sleeps 12

Lakefront Paradise Pool + Paddle Boats Sleeps 12
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful week long stay. The house is beautiful and right on the lake, with beautiful views and sunsetsWe were there for a West Point Graduation and was about a 30 minute drive to the school, even on the busy days of the parade and graduation dayThe house had plenty of room for our group and the host was easy to get ahold of. There are 4 official bedroom and 4 bathrooms and a basement and 2 office/den, 2 washer and dryers - one in the top floor and another in the basement which has...
United States
Courtney D.
The price is £1,506
includes taxes & fees
5 Aug - 6 Aug
Lakefront Paradise Pool + Paddle Boats Sleeps 12
Coffee/tea maker, fridge, microwave, oven

Amazing Home Near West Point, Shopping, Skiing and Legoland

Amazing Home Near West Point, Shopping, Skiing and Legoland
Monroe
10.0 out of 10, Exceptional, (14 reviews)
"The host was welcoming and easy to reach. It’s a lovely, fully stocked house that had everything we needed. Check-in and check-out were a breeze. Nice, quiet location."
United States
Michael M.
The price is £374
includes taxes & fees
24 Jul - 25 Jul
Amazing Home Near West Point, Shopping, Skiing and Legoland
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

8/10 Good
"Bed was very comfortable and room was well air conditioned. Room and bathroom were very small and “no frills”. Just the bare minimum. Continental breakfast was a small selection. Good for an inexpensive stay."
Lorraine 2-night trip
Posted 11 hours ago
Spark by Hilton Fishkill

Find out more about Chester

Chester Holiday Homes information

Number of reviews
197
Accommodation
352 Holiday Homes
Lowest Price
£246
Highest Price
£3,905