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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chester vacation homes

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, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥21,677
￥64,745 total
includes taxes & fees
Jun 30 - Jul 1
House on the Babbling Brook- Quiet 2BR + King Bed!
Interior

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (12 reviews)
"The bed was very comfortable! Loved the sitting area in the room! The downstairs of this location is an excellent restaurant! "
United States
Annette L.
The price is ￥14,414
￥25,091 total
includes taxes & fees
Jul 6 - Jul 7
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
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 convenient stay for a few days in the mountain!!! "
United States
rebecca l.
The price is ￥23,149
￥49,488 total
includes taxes & fees
Jul 6 - Jul 7
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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, (9 reviews)
"So cute and cozy!! We had the best time and loved it. "
United States
corinne n.
The price is ￥43,516
￥80,641 total
includes taxes & fees
Jul 22 - Jul 23
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
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)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is ￥27,986
￥83,085 total
includes taxes & fees
Jun 30 - Jul 1
3BR West Point Retreat-3min to Back Gate+ King Bed
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥36,398
￥68,459 total
includes taxes & fees
Jun 28 - Jun 29
Contemporary Cozy Cottage
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, (58 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 ￥32,742
￥68,380 total
includes taxes & fees
Jul 12 - Jul 13
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
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, (68 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is ￥40,038
￥52,281 total
includes taxes & fees
Jul 7 - Jul 8
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior

Private Mountain Creek Getaway!

Private Mountain Creek Getaway!
Vernon Township
9.0 out of 10, Wonderful, (7 reviews)
"This place is fantastic, Charlie was extremely helpful and went above and beyond to ensure our stay was satisfactory. This place includes a lot in your stay such as towels soap/shampoo and even cotton swabs. This place is a great location and will 100% recommend for anyone staying in the area. We will definitely book again at this place and so should you if you want privacy and a great stay with a fantastic host. Thank You Charlie for the warm welcome."
United States
Cristian S.
The price is ￥29,046
￥67,903 total
includes taxes & fees
Jun 28 - Jun 29
Private Mountain Creek Getaway!
TV

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (8 reviews)
"Nice, clean little property in a secluded area. Great to get away."
United States
David F.
The price is ￥31,060
￥66,999 total
includes taxes & fees
Jun 28 - Jun 29
Hike & Fish: Outdoor Retreat Near Trails
Smart TV, offices, printers

Highland Lakes Cabin | Huge Yard • Sleeps 8

Highland Lakes Cabin | Huge Yard • Sleeps 8
Highland Lakes
10.0 out of 10, Exceptional, (10 reviews)
"We loved this rental! Very charming and clean and will definitely return. "
United States
Devorah K.
The price is ￥29,800
￥77,876 total
includes taxes & fees
Jun 30 - Jul 1
Highland Lakes Cabin | Huge Yard • Sleeps 8
Fridge, microwave, oven, stovetop

3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (2 reviews)
"A friend and I needed to book a last minute stay. This house exceeded our expectations. It was clean and comfortable and had everything we needed. It was a great location as well!"
United States
Rachel S.
The price is ￥42,572
￥94,724 total
includes taxes & fees
Jun 28 - Jun 29
3BR Hudson Valley home perfect for families!
Interior

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is ￥43,134
￥49,431 total
includes taxes & fees
Jul 19 - Jul 20
Harriman Outdoor Center - Cranberry Cabin
Dining

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
Monroe
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy home in a quiet and safe neighborhood. "
United States
Jillian C.
The price is ￥40,766
￥120,433 total
includes taxes & fees
Jun 26 - Jun 27
Family Home Close to Warwick, 5 Mi to Lake!
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, (38 reviews)
"We have stayed here a few times and the house is always perfect. Will stay here again in the future! "
United States
Lex S.
The price is ￥41,251
￥94,612 total
includes taxes & fees
Jun 29 - Jun 30
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Interior

Lux Lake Neepaulin Frontage & Panoramic Views Home

Lux Lake Neepaulin Frontage & Panoramic Views Home
Wantage
7.8 out of 10, Good, (9 reviews)
"Nice place to stay. "
United States
Bob
The price is ￥32,354
￥44,446 total
includes taxes & fees
Jun 29 - Jun 30
Lux Lake Neepaulin Frontage & Panoramic Views Home
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 ￥48,919
￥82,997 total
includes taxes & fees
Jul 7 - Jul 8
Lovely 3BR Home with parking-Walk to WP Gate!
Dining

Serene Rustic Retreat with Lake

Serene Rustic Retreat with Lake
Cuddebackville
10.0 out of 10, Exceptional, (8 reviews)
"Amazing stay and beautiful home!"
United States
Koby A.
Serene Rustic Retreat with Lake
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.6 out of 10, Exceptional, (7 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ￥47,835
￥78,546 total
includes taxes & fees
Jul 14 - Jul 15
Fabulous 3bdrm Home w/parking!
Fridge, microwave, stovetop, dishwasher

Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful place, safe neighborhood, very clean and cozy. "
United States
Glori B.
Bright Cornwall-On-Hudson Vacation Rental!
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

10/10 Excellent
"The staff I came across were great and very helpful. I would stay here again if in the area."
Patricia 1-night trip
Posted 1 hour ago
Spark by Hilton Fishkill

Find out more about Chester

Chester Vacation Homes information

Number of reviews
314
Accommodation
371 Vacation Homes
Lowest Price
￥25,091
Highest Price
￥120,433