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Compare 261 Vacation Homes in Chester with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (27)
"Weather was not so great to be outside but the game room made up for it!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop
New 5 Bedrm, 3bath with Swim Spa and Huge Outdoor Space
10.0 out of 10, Exceptional, (13)
"We stayed at JT's property for a weekend in November to attend a football game at the military academy at West Point. Seven of us, including 3 teenagers, had plenty of space to be comfortable, relax, cook meals and enjoy the swim spa. The home was warm and clean and we all slept great. We'll definitely look to stay there again whenever we need lodging near West Point."
New 5 Bedrm, 3bath with Swim Spa and Huge Outdoor Space
Microwave, oven, dishwasher
LOCATION ! This unique property is walking distance to the Village of Warwick!
10.0 out of 10, Exceptional, (1)
"Hosts welcomed us with cookies from Noble Pies, milk for my young child and dog supplies for my two dogs. Hosts were easy to reach and communicate with. Home has all you need to enjoy a short or long stay!"
LOCATION ! This unique property is walking distance to the Village of Warwick!
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Fridge, microwave, stovetop, dishwasher
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (2)
"We had an enjoyable stay. Easy check in and house was exactly as noted in listing. Super convenient for access to West Point. No issue for my group, but stairs are steep and could be a challenge for some people. We would / will stay again next time in the area."
Bright Cornwall-On-Hudson Vacation Rental!
Property grounds
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (127)
"This was our 2nd stay and even better, as this time we explored the woods behind the house where a brook runs back far enough we never found the end or edge of the property. Great hikes less than 20 min drive away, but honestly exploring the woods and stream was about our speed, with teens who are non-experienced hikers. Used the hot tub every night under the stars, built fires and did s'mores multiple times in the fire pit. Large porch with ping pong, foosball, keyboard and movie watching spot...
Beautiful Private Stone Home in the Hudson Valley
Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (114)
"EXCELLENT"
Lakefront Luxury on Greenwood Lake
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (2)
"The property was beautiful and just as pictured. The host was more than attentive and helpful. He went above and beyond to make sure my stay was fantastic. I highly recommend this property!"
Cozy family-friendly home!
Fireplace
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (1)
"A very short but pleasant stay and the host gave us good communication."
The price is $250
$377 total
includes taxes & fees
May 20 - May 21
Contemporary Cozy Cottage
Outdoor spa tub
Lakefront/Legoland/Mt. Peter Retreat Under 1 Hour From NYC! Heated pool & Spa!
10.0 out of 10, Exceptional, (27)
"We had a lovely vacation at Ilya’s. Beautiful setting and so close to the city which was a huge plus!"
Lakefront/Legoland/Mt. Peter Retreat Under 1 Hour From NYC! Heated pool & Spa!
Property grounds
Lake Front Home close to Great Hiking Trails & just 60 minutes from NYC
10.0 out of 10, Exceptional, (3)
"Enjoyed quality time spent with daughter. Cute bungalow house in nice historical neighborhood, safe location and amazing views of the lake. Close to Beacon, New Paltz, Warwick, Walden and other cute little towns. 5 stars 💛"
Lake Front Home close to Great Hiking Trails & just 60 minutes from NYC
Smart TV, fireplace, video games, table tennis
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
10.0 out of 10, Exceptional, (3)
"Great experience. Liked the location. Only complaint needs more hangers in the closets. Nice stay for big grouos"
The price is $444
$822 total
includes taxes & fees
May 8 - May 9
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
Fridge, microwave, oven, stovetop
Contemporary Cottage less than an hour from NYC!
10.0 out of 10, Exceptional, (16)
"Near our family in NJ. Close to the city, very quiet neighborhood."
Contemporary Cottage less than an hour from NYC!
Fridge, microwave, oven, stovetop
The Sweet Spot: Fun-Filled Summer Getaway
10.0 out of 10, Exceptional, (4)
"Our family (kids/spouse/grand) came together here from 4 different states. Warm cozy n large enough for the 9 of us...wish our stay was longer."
The Sweet Spot: Fun-Filled Summer Getaway
Private kitchen
Spacious Port Jervis Home - beautiful views
10.0 out of 10, Exceptional, (1)
"Clean, spacious and beautiful property. Would definitely stay again if in the area."
Spacious Port Jervis Home - beautiful views
Fridge, microwave, stovetop, dishwasher
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
10.0 out of 10, Exceptional, (21)
"This is an attractive, well-laid out house with an extremely accommodating owner. The home is pretty small—great for two or three with very little play area inside for kids—but there are several great outside areas on the deck, around the pool and stream. In terms of accessibility, three steps up to the doorway, a step down to the master bedroom and a step up to the ensuite master bath."
Updated Getaway w/ Pool & Hot Tub on 2.5 Acres!
Fridge, microwave, oven, stovetop
Amazing Home Near West Point, Shopping, Skiing and Legoland
10.0 out of 10, Exceptional, (7)
"Perfect for what we needed. Quiet neighborhoid"
The price is $350
$564 total
includes taxes & fees
May 18 - May 19
Amazing Home Near West Point, Shopping, Skiing and Legoland
Fridge, microwave, oven, stovetop
Waterfront Modern Home w/Fast Wifi & 400m from DT
10.0 out of 10, Exceptional, (1)
"We loved our stay. The home is very clean and comfortable. The view of the lake is excellent, and we had the great experience of waking up to watching swans swimming. The location is excellent for a walk into town. Jack is also quick to respond to messages, and the check in and check out process was very easy. Great stay!"
The price is $185
$433 total
includes taxes & fees
May 8 - May 9
Waterfront Modern Home w/Fast Wifi & 400m from DT
Snow and ski sports
10 minutes away from Mountain Creek, beautiful spacious house with Mountain View
10.0 out of 10, Exceptional, (6)
"This was a beautiful home and the hosts were SO GREAT! Available for immediate contact, so kind and helpful, and left many wonderful touches in the home to greet us. The house has so many fun things to do and the beds were the most comfortable we have ever had in a rental. Everything felt extremely clean which is huge for us! I thought hiking would have been easier access on foot, but plan to drive to any hikes (not far!). Gorgeous home w great owners!"
The price is $230
$548 total
includes taxes & fees
May 6 - May 7
10 minutes away from Mountain Creek, beautiful spacious house with Mountain View
Fridge, microwave, oven, stovetop
Newly Renovated Gorgeous Home in Goshen
9.8 out of 10, Exceptional, (31)
"With extended family in this area, we have stayed in several local rentals while visiting relatives and this one is near the top. The home is newly renovated and clean, the property is beautiful, and the area is very peaceful. This is a great find and I would highly recommend."
Newly Renovated Gorgeous Home in Goshen
View from property
‘The Point on Highland Lake’ Near Mtn Creek Resort
9.8 out of 10, Exceptional, (53)
"We stayed for a long weekend to celebrate my son’s 14th birthday. The house is tastefully decorated and feels newly renovated. The location is lovely! Perfect spot for a relaxing stay."
‘The Point on Highland Lake’ Near Mtn Creek Resort
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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.

Other property types in Chester

Chester Vacation Homes information

Number of reviews
437
Accommodation
261 Vacation Homes
Lowest Price
$185
Highest Price
$444

Recent reviews of Chester hotels
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