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Our top choices for Chester vacation 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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 261
AED 1,183 total
includes taxes & fees
29 Jan - 30 Jan
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
9.2 out of 10, Wonderful, (9 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 AED 334
AED 577 total
includes taxes & fees
9 Feb - 10 Feb
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3 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 AED 455
AED 1,596 total
includes taxes & fees
1 Feb - 2 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Hidden Lakefront Gem on a Gated Countryside Escape

Hidden Lakefront Gem on a Gated Countryside Escape
2.0 star property
Monroe
The price is AED 321
AED 832 total
includes taxes & fees
29 Jan - 30 Jan
Hidden Lakefront Gem on a Gated Countryside Escape

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)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
The price is AED 404
AED 1,608 total
includes taxes & fees
29 Jan - 30 Jan
3BR West Point Retreat-3min to Back Gate+ King Bed

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 AED 641
AED 1,252 total
includes taxes & fees
29 Jan - 30 Jan
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 644
AED 1,211 total
includes taxes & fees
4 Feb - 5 Feb
Fabulous 3bdrm Home w/parking!

Marvelous 6-bedroom house with AC in Monroe

Marvelous 6-bedroom house with AC in Monroe
Monroe
Marvelous 6-bedroom house with AC in Monroe

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, (59 reviews)
"Clean and comfortable accommodations, very close to Legoland and Castle Fun Center! The kids loved the room with bunk beds, and it had a big selection of children's books and some toys, which was a nice bonus!"
United States
Jennifer K.
The price is AED 909
AED 1,828 total
includes taxes & fees
29 Jan - 30 Jan
Country House w/Hot Tub, Deck, Grill & Fire Pit

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 AED 826
AED 1,554 total
includes taxes & fees
29 Jan - 30 Jan
Contemporary Cozy Cottage

Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle
Monroe
8.0 out of 10, Very Good, (3 reviews)
"Yes, everything was lovely"
United States
Tiffanie C.
The price is AED 470
AED 1,550 total
includes taxes & fees
2 Feb - 3 Feb
Scenic View - WiFi - Fire Pit - Near Legoland, Woodbury Commons and the Castle

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, (48 reviews)
"Great place to stay!"
United States
Michele B.
The price is AED 526
AED 1,116 total
includes taxes & fees
1 Feb - 2 Feb
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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, (3 reviews)
"We had a great time staying here. It was very clean and the view was amazing. Wanted to meet up with some family and it was perfect for relaxing and catching up. Host accommodated our early check in request and was available during our stay when we had minor questions. Overall, it was wonderful."
United States
Joe K.
The price is AED 793
AED 1,549 total
includes taxes & fees
29 Jan - 30 Jan
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

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
9.4 out of 10, Exceptional, (57 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is AED 909
AED 1,157 total
includes taxes & fees
29 Jan - 30 Jan
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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, (33 reviews)
"Beautiful property, the photos do it justice, but the location (and peace) of the property can't be seen in just pictures. The family agreed one of the best places we've gotten, wonderful way to spend a late summer week on the lake."
United States
Devan S.
The price is AED 663
AED 1,780 total
includes taxes & fees
29 Jan - 30 Jan
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

NEW 5 Trinity Pl Cornwall NY 12518

NEW 5 Trinity Pl Cornwall NY 12518
2.0 star property
Cornwall
The price is AED 1,969
AED 4,384 total
includes taxes & fees
2 Feb - 3 Feb
NEW 5 Trinity Pl Cornwall NY 12518

Charming bungalow in lovely Middletown NY

Charming bungalow in lovely Middletown NY
Middletown
The price is AED 496
AED 716 total
includes taxes & fees
29 Jan - 30 Jan
Charming bungalow in lovely Middletown NY

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 AED 677
AED 1,565 total
includes taxes & fees
29 Jan - 30 Jan
Private Mountain Creek Getaway!

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is AED 735
AED 1,180 total
includes taxes & fees
1 Feb - 2 Feb
Luxury House Near West Point

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room

Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
West Milford
10.0 out of 10, Exceptional, (4 reviews)
"The property was spotless, comfortable, and had everything we needed. The location was perfect—close to attractions yet quiet and relaxing. The hosts were amazing, welcoming and very responsive, they were welling to help us at all times and they may made sure the whole experience was smooth and enjoyable. We’d definitely stay here again!"
United States
Bana S.
The price is AED 1,006
AED 2,054 total
includes taxes & fees
29 Jan - 30 Jan
Lakefront Haven • Ski at Mt. Peter, Mountain Creek • Dock • Fire Pit • Game Room
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