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Compare 311 Vacation Homes in Chester with updated reviews, rates, and availability.

Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (116)
"This is our second visited and we are still in love with the Lake House!"
Lakefront Luxury on Greenwood Lake
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
10.0 out of 10, Exceptional, (22)
"My family and I had a wonderful weekend at the property. It rained most of the time, but we made the best of it. It was all over too fast. It's a nice, relaxing property."
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
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Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (12)
"Great location and communication! Very clean and nice!"
The price is SAR 598
SAR 1,207 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay at this beautiful and quaint home in the heart of the Cornwall village. The house was exactly as described, communication with the host was easy and quick, and we enjoyed being so close to everything Cornwall has to offer. We would absolutely recommend this beautiful home for your next visit to the Cornwall area"
Bright Cornwall-On-Hudson Vacation Rental!
Lake House, ONE HOUR from NYC
9.8 out of 10, Exceptional, (23)
"Great place and Rhona did a great job (great communication, timely, and adaptable). Well done!"
Lake House, ONE HOUR from NYC
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
10.0 out of 10, Exceptional, (9)
"Had a great time at this house. It is perfect for large groups and had so many great amenities. Doug was extremely responsive and helpful. Highly recommend!"
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
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
Great hikes, Crystal Springs Spa, 1 block off the lake & Pet Friendly!
9.6 out of 10, Exceptional, (10)
"This sweet house is perfect! Great yard with a fire pit and fenced in for dogs Very clean and well appointed. Quiet neighborhood with walkable streets down to the lake. I look forward to staying again"
Great hikes, Crystal Springs Spa, 1 block off the lake & Pet Friendly!
12 Private Acres with pristine Views of the Gunks
9.6 out of 10, Exceptional, (70)
"We were a party of 5, myself and my husband with our three 20 something kids. The house is modest from the exterior but the interior is very special. Old wide pine floors and wood beamed ceilings - very unexpected! Everything we needed was there, comfortable furnishings and a tv to watch the basketball games. The property itself is gorgeous, with a waterfall in the backyard and expansive lawn. It's a short walk or drive to a lake with other lakes and hikes nearby. Very private area. Three...
12 Private Acres with pristine Views of the Gunks
CREATIVES DREAM GETAWAY
10.0 out of 10, Exceptional, (1)
"Our group of 4 adults spent 3 nights in Ezequiel's beautiful property. It was cozy, beautifully decorated, comfortable, and the kitchen had everything you could possibly need. We enjoyed the lovely, tranquil outdoor space, and we had easy access to the attractions we were there to visit (Mohank Nature Preserve, CIA -Culinary Institute of America, Storm King Sculpture Park, etc.). Highly recommend and would definitely stay here again."
CREATIVES DREAM GETAWAY
The Woodbury Cottage
10.0 out of 10, Exceptional, (1)
"We really enjoyed relaxing on the front porch after a busy day out. Beds were very comfortable. So nice to be able to sit around and visit, instead being in a hotel, sitting on beds. We did miss having a microwave to use. Very nice and affordable."
The Woodbury Cottage
Red Cabin Lake House with Amazing Views!
2.0 out of 10, (1)
"Fishing/Lake: There is absolutely no access to the lake, including the community beach. No swimming. No fishing. Such details must be in the property's details in caps. Fishing or swimming is not allowed. Water: Smelly brown water in the house. You can’t drink it or cook with it or even take a shower. It is disguising. No heads-up about the water issue. Kitchen: The smell of dirty dishes welcomed us. It looks like the previous renters left them there. Only 4 forks and 1 knife in the house....
Red Cabin Lake House with Amazing Views!
Hudson valley remodel bilevel@Brendella court
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at Gloria's house! Communication was excellent, and she provided a great list of local restaurants. The house was well-stocked with energy bars, drinks, and fruits, which made our stay very comfortable. We enjoyed every moment and had a very pleasant stay."
The price is SAR 1,125
SAR 1,287 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Hudson valley remodel bilevel@Brendella court
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (31)
"We came for West Point graduation. It was perfect in its location to West Point. Beds were good, its was very clean, and the hot tub was great! The owners communicated well and helped us with our scheduling. We highly recommend this place!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (2)
"A very short but pleasant stay and the host gave us good communication."
The price is SAR 938
SAR 1,410 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Contemporary Cozy Cottage
3 bedroom country home off hiking trail
8.6 out of 10, Excellent, (8)
"The house was an older cute home. Very comfortable and inviting. The owner Tony was very easy to talk with and a great communicator. The kitchen is lovely and had plenty of things for your need. We really enjoyed our stay! 😊"
The price is SAR 454
SAR 1,601 total
includes taxes & fees
3 Jum. II - 4 Jum. II
3 bedroom country home off hiking trail
5 Acre Modern Mountain Farm
9.4 out of 10, Exceptional, (19)
"Property was what we expected. Very nice quiet area, lots of room in the house to make all of us 8 adults feel comfortable, like plenty of room on the outside deck… There are minor things that could be addressed, which I’m sure they are well aware. I would recommend for a group that just wants to get away and relax. "
5 Acre Modern Mountain Farm
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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

Cottage Suites
3.0 star property
8.0 out of 10, Very Good, (1)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is SAR 705
SAR 998 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
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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