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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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ¥22,437
¥64,574 total
includes taxes & fees
May 11 - May 12
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)
"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 ¥12,991
¥23,218 total
includes taxes & fees
May 12 - May 13
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is ¥31,380
¥50,928 total
includes taxes & fees
May 10 - May 11
Luxury House Near West Point

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is ¥31,223
¥37,400 total
includes taxes & fees
May 10 - May 11
Luxury home near West Point

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 ¥38,833
¥51,252 total
includes taxes & fees
May 13 - May 14
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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 ¥25,732
¥75,327 total
includes taxes & fees
May 11 - May 12
Sleek Escape: Modern 3 BR- 4 Min from West Point !

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, (62 reviews)
"Very good host "
United States
Binyomin
The price is ¥40,559
¥80,675 total
includes taxes & fees
May 10 - May 11
Country House w/Hot Tub, Deck, Grill & Fire Pit

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 ¥26,651
¥63,443 total
includes taxes & fees
May 13 - May 14
Private Mountain Creek Getaway!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is ¥33,937
¥59,970 total
includes taxes & fees
May 11 - May 12
Fabulous 3bdrm Home w/parking!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Warwick
10.0 out of 10, Exceptional, (5 reviews)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is ¥32,026
¥71,905 total
includes taxes & fees
May 17 - May 18
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

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)
"Nice stay, with accommodations as described."
United States
Matthew K.
The price is ¥22,452
¥47,685 total
includes taxes & fees
May 10 - May 11
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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 ¥37,397
¥66,342 total
includes taxes & fees
May 10 - May 11
Lovely 3BR Home with parking-Walk to WP Gate!

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)
"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 ¥30,596
¥63,201 total
includes taxes & fees
May 11 - May 12
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (33 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ¥39,170
¥71,322 total
includes taxes & fees
Jun 9 - Jun 10
Contemporary Cozy Cottage

⛷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 ¥40,033
¥66,436 total
includes taxes & fees
May 19 - May 20
⛷Modern 3bd2bth, walk to SPA & dining

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)
"Second time staying here. Check in is a smooth process. House has everything we needed! "
United States
Lex S.
The price is ¥41,579
¥93,540 total
includes taxes & fees
May 27 - May 28
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Lakefront Haven • Private Dock • Private Beach • Fire Pit • Game Room

Lakefront Haven • Private Dock • Private Beach • Fire Pit • Game Room
West Milford
10.0 out of 10, Exceptional, (5 reviews)
"A very clean and wonderful place, where we enjoyed a peaceful weekend with our family. We absolutely loved it. Highly recommended for everyone."
United States
Johana
The price is ¥42,987
¥87,420 total
includes taxes & fees
May 10 - May 11
Lakefront Haven • Private Dock • Private Beach • Fire Pit • Game Room

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 ¥23,849
¥32,832 total
includes taxes & fees
May 26 - May 27
Lux Lake Neepaulin Frontage & Panoramic Views Home

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 ¥30,100
¥63,584 total
includes taxes & fees
May 11 - May 12
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!

Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!
Warwick
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay at this beautiful property. The host was super responsive and very accommodating. The house is on secluded grounds and there is lots of privacy. We were very comfortable. A great place to stay with the family. "
United States
Anna D.
The price is ¥47,785
¥108,548 total
includes taxes & fees
Jun 1 - Jun 2
Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!
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 Vacation Homes information

Number of reviews
359
Accommodation
313 Vacation Homes
Lowest Price
¥23,218
Highest Price
¥108,548