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Compare 293 Vacation Homes in Chester with updated reviews, rates, and availability.

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.6 out of 10, Exceptional, (23)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is SAR 598
SAR 1,225 total
includes taxes & fees
3 Feb - 4 Feb
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Spacious Getaway! 7BR w Park & pool Scenic Views

Spacious Getaway! 7BR w Park & pool Scenic Views

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is SAR 971
SAR 1,106 total
includes taxes & fees
8 Feb - 9 Feb
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Majestic RiverView Estate - Breathtaking Views

10.0 out of 10, Exceptional, (4)
"We booked a weekend away to celebrate family birthdays and were very happy to celebrate in such a special place. There was plenty of room for 11 of us (+ dog) and was a mix of modern touches and old world charm highlighting the legacy of the house. And the view of the Hudson was a highlight of our stay. Highly recommend!"
Majestic RiverView Estate - Breathtaking Views

Cozy Indoor Hot Tub, Fire Pit & Game Room

9.6 out of 10, Exceptional, (4)
"It was a wonderdul and relaxing stay with the family"
Cozy Indoor Hot Tub, Fire Pit & Game Room

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!

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (1)
"Alexis was a great host and she was super communicative and easy to reach. The house was clean and prefect size for my group of 6. Most things were stocked but I’d reach out to the host in advance so you can buy anything that isn’t ahead of time. One important thing to note is that the driveway can only fit 2 cars and there isn’t really any street parking. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (14)
"House is spacious and clean. The little touches like the Christmas decorations, games, books etc. were greatly appreciated. Beautiful property. Would definitely return. "
Catskills mountain gateway house.

Vernon Cozy 2BD Pet-Friendly Mountain Creek

8.0 out of 10, Very Good, (1)
The price is SAR 330
SAR 1,140 total
includes taxes & fees
12 Feb - 13 Feb
Vernon Cozy 2BD Pet-Friendly Mountain Creek

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (12)
"Property was better than advertised and exceeded all our expectations. All aspects of the VRBO process with the owner and management company were seamless. Highly recommend and will stay there again."
Bright Cornwall-On-Hudson Vacation Rental!

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

The Perfect up to date Private Getaway to call home for a while

8.6 out of 10, Excellent, (4)
"This property and listing was perfect for our men's retreat weekend getaway. We gathered together and enjoyed being able to spread out in the spacious home. It was very close to a local park with a pool, basketball court, and open field. We also enjoyed grilling on the patio and using the fire-pit to roast s'mores in the evening. The driveway had plenty of parking. The pool on the property was unusable but the backyard was perfect for us to play football and have outdoor activities. We...
The Perfect up to date Private Getaway to call home for a while

Delightful Home w/ Fire Pit, Walk to Lake!

9.8 out of 10, Exceptional, (9)
"This was a cute house in a beautiful spot of NY. It was cozy and well taken care off. The neighborhood was quiet and beautiful also. We would come agian. "
Delightful Home w/ Fire Pit, Walk to Lake!

Up-to-date Home w/ Pool, Playground & Fireplace!

10.0 out of 10, Exceptional, (1)
Up-to-date Home w/ Pool, Playground & Fireplace!

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

10.0 out of 10, Exceptional, (24)
"Would stay here again "
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (23)
"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "
Updated Home w/ Patio Half Mile to West Point

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (38)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

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!
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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Other property types in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is SAR 630
SAR 923 total
includes taxes & fees
6 Feb - 7 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.6 out of 10, Exceptional, (23)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is SAR 598
SAR 1,225 total
includes taxes & fees
3 Feb - 4 Feb
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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.