Holiday Homes in Chester

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday Homes in Chester and around

Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
United States
Scott G.
The price is €329
includes taxes & fees
21 Oct - 22 Oct
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
9.6 out of 10, Exceptional, (4)
"The Warwick Inn is an amazing stay for anyone trying to escape for a few days. The rooms were amazing, spacious, and comfortable. Gabriela was amazing at setting up our check-in and was always available for any questions we had. Highly recommend. "
United States
Nicolas
The price is €133
includes taxes & fees
21 Oct - 22 Oct
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior
Lovely 3BR Home with parking-Walk to WP Gate!
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (6)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
United States
Molly s.
The price is €274
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!
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
9.4 out of 10, Exceptional, (40)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
United States
Louise S.
The price is €267
includes taxes & fees
24 Oct - 25 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Fridge, microwave, oven, stovetop
Fabulous 3bdrm Home w/parking!
Fabulous 3bdrm Home w/parking!
8.0 out of 10, Very good, (2)
"Great place. Close to West Point activity. Clean and new."
United States
Joanne V.
The price is €250
includes taxes & fees
21 Oct - 22 Oct
Fabulous 3bdrm Home w/parking!
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed
3BR West Point Retreat-3min to Back Gate+ King Bed
9.0 out of 10, Wonderful, (2)
"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 €435
includes taxes & fees
27 Oct - 28 Oct
3BR West Point Retreat-3min to Back Gate+ King Bed
Property grounds
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
2.0 star property
10.0 out of 10, Exceptional, (2)
"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 €359
includes taxes & fees
2 Nov - 3 Nov
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Dining
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
9.8 out of 10, Exceptional, (58)
"We had a wonderful stay! The house is in a beautiful location, everything was well appointed, instructions were easy to follow and the house itself was perfect. "
United States
Katie
The price is €492
includes taxes & fees
21 Oct - 22 Oct
Renovated House w/Hot Tub, Deck, Grill & Fire Pit
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (1)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is €420
includes taxes & fees
29 Oct - 30 Oct
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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
9.8 out of 10, Exceptional, (41)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is €290
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Lux Lake Neepaulin Front Home
Lux Lake Neepaulin Front Home
8.0 out of 10, Very good, (2)
"Nice place to stay. "
United States
Bob
The price is €263
includes taxes & fees
27 Oct - 28 Oct
Lux Lake Neepaulin Front Home
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (56)
"Loved this property, clean, wonderful view of the river. Quite neighborhood. Great location "
United States
Mamie G.
The price is €347
includes taxes & fees
26 Oct - 27 Oct
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Interior
Charming bungalow in lovely Middletown NY
Charming bungalow in lovely Middletown NY
The price is €171
includes taxes & fees
21 Oct - 22 Oct
Charming bungalow in lovely Middletown NY
Exterior
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!
10.0 out of 10, Exceptional, (7)
"We enjoy our stay at this beautiful home. The house is very spacious and clean. It is located in a great area and was very quiet."
United States
matthew l.
Secluded Warwick Retreat on 3 Acres Next to Winery- 1 Hr from NYC!
Exterior
West Point Family Retreat, 5 min walk to Thayer!
West Point Family Retreat, 5 min walk to Thayer!
2.0 star property
9.8 out of 10, Exceptional, (6)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
United States
Randall T.
The price is €727
includes taxes & fees
21 Oct - 22 Oct
West Point Family Retreat, 5 min walk to Thayer!
Interior
Contemporary Cozy Cottage
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (28)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is €372
includes taxes & fees
21 Oct - 22 Oct
Contemporary Cozy Cottage
Exterior
Lake House in the Forest
Lake House in the Forest
10.0 out of 10, Exceptional, (2)
"We were so happy to get away to the mountains for this Spring Break! The property was so quiet and peaceful. Just what we needed to re-charge. We loved kayaking and canoeing each day and making smores by the fire. The dock was a beautiful place to watch the sunset over the lake. Wonderful hosts. We couldn't ask for anything more!"
United States
Kristin S.
The price is €351
includes taxes & fees
21 Oct - 22 Oct
Lake House in the Forest
Fridge, microwave, oven, stovetop
Private Mountain Creek Getaway!
Private Mountain Creek Getaway!
8.4 out of 10, Very good, (5)
"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 €390
includes taxes & fees
23 Oct - 24 Oct
Private Mountain Creek Getaway!
Interior
Large,Cozy,Bright Apartment, Business Themed.
Large,Cozy,Bright Apartment, Business Themed.
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is €607
includes taxes & fees
21 Oct - 22 Oct
Large,Cozy,Bright Apartment, Business Themed.
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Clean beautiful room and properties "
Brian 1-night trip
Posted 2 days ago
Crowne Plaza Suffern - Mahwah by IHG

Find out more about Chester

Chester Holiday Homes information

Number of reviews
270
Accommodation
328 Holiday Homes
Lowest Price
€133
Highest Price
€727