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Our top choices for Chester holiday homes

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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is £292
includes taxes & fees
3 Jun - 4 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!

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, (16 reviews)
"The host was very helpful and considerate, the rooms was nice."
United States
David A.
The price is £145
includes taxes & fees
9 Jun - 10 Jun
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

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, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is £240
includes taxes & fees
5 Jun - 6 Jun
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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 £315
includes taxes & fees
3 Jun - 4 Jun
Contemporary Cozy Cottage

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 £378
includes taxes & fees
7 Jun - 8 Jun
3BR West Point Retreat-3min to Back Gate+ King Bed

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 £310
includes taxes & fees
3 Jun - 4 Jun
Private Mountain Creek Getaway!

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)
"Great location and super host. "
United States
James U.
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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 £230
includes taxes & fees
5 Jun - 6 Jun
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.8 out of 10, Exceptional, (7 reviews)
"Nice, clean little property in a secluded area. Great to get away."
United States
David F.
The price is £331
includes taxes & fees
3 Jun - 4 Jun
Hike & Fish: Outdoor Retreat Near Trails

Big Stone House in Charming Catskills Village

Big Stone House in Charming Catskills Village
Wurtsboro
6.4 out of 10, (5 reviews)
"It was a great time"
United States
cesar s.
The price is £297
includes taxes & fees
3 Jun - 4 Jun
Big Stone House in Charming Catskills Village

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 £293
includes taxes & fees
7 Jun - 8 Jun
Fabulous 3bdrm Home w/parking!

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 £355
includes taxes & fees
3 Jun - 4 Jun
3BR Hudson Valley home perfect for families!

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 £335
includes taxes & fees
10 Jun - 11 Jun
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

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, (37 reviews)
"Great communication with the host and its a beautiful home. Very clean and a great location with wonderful views."
United States
Frank M.
The price is £388
includes taxes & fees
9 Jun - 10 Jun
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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 £537
includes taxes & fees
10 Jun - 11 Jun
Family Home Close to Warwick, 5 Mi to Lake!

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 £301
includes taxes & fees
7 Jun - 8 Jun
Lovely 3BR Home with parking-Walk to WP Gate!

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
Greenwood Lake
10.0 out of 10, Exceptional, (10 reviews)
"Very nice location and very responsive host to a few issues we encountered. Appreciated the flexibility with accommodating a later check out. We would stay here again!"
United States
Baljit P.
The price is £522
includes taxes & fees
8 Jun - 9 Jun
Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Harriman Outdoor Center - Cranberry Cabin

Harriman Outdoor Center - Cranberry Cabin
Haverstraw
The price is £211
includes taxes & fees
4 Jun - 5 Jun
Harriman Outdoor Center - Cranberry Cabin

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (64 reviews)
"Very good host "
United States
Binyomin
The price is £447
includes taxes & fees
3 Jun - 4 Jun
Country House w/Hot Tub, Deck, Grill & Fire Pit

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, (10 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 £120
includes taxes & fees
8 Jun - 9 Jun
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
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

Find out more about Chester

Chester Holiday Homes information

Number of reviews
342
Accommodation
335 Holiday Homes
Lowest Price
£120
Highest Price
£537