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Compare 23 Villas in Chester with updated reviews, rates, and availability.

Luxury 5-Bdrm Getaway Near West Point

3.0 star property
10.0 out of 10, Exceptional, (1)
"This property was fantastic!! The house was beautiful and spacious for our family! The master bathroom had a really cool shower and the kids enjoyed the game room. There were seperate thermostats that everyone can enjoy their own temperature. The views were stunning and the neighborhood was quiet!The host was easy to deal with and communicated in a timely response!!I would highly recommend this property and host! We would totally book again!communit"
Luxury 5-Bdrm Getaway Near West Point

Luxurious Villa with pool spa arcade room and more

10.0 out of 10, Exceptional, (5)
"Warm, roomy, and quiet. Lots of room for our family of 5. Communication with host was amazing."
Luxurious Villa with pool spa arcade room and more

MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

9.6 out of 10, Exceptional, (12)
"I loved the house, I'll be back for sure"
MODERN FARMHOUSE HOME ON 5-ACRE DREAM PROPERTY

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

9.2 out of 10, Wonderful, (7)
"A spacious house with a to-die-for pool, game room in basement, plenty of storage and refrigerators for all your wonderful culinary desires, comfortable beds, and well divided together and private spaces."
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

2.0 out of 10, (1)
"There was rats inside the house and there was no amenities like toilet paper. And host was very unresponsive."
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

10.0 out of 10, Exceptional, (1)
"This house was absolutely perfect for our friend's weekend wedding. 14 guests, guys/girls in their early to mid 30s. We stayed at this house and attended our friend's rehearsal dinner and wedding about 30 min away. The location is perfect, slightly secluded and quiet. The property is very large and has all the amenities a group of people could want. The interior of the house was clean, setup nicely, and aesthetically pleasing. Everything listed was accurate. The pool and hot tub were clean and...
DREAM Home, Pool, Hot Tub, Game Rm & Mountains.

Fully facilitated home, 7 Beds + Pool. (Pine Bush)

3.4 out of 10, (3)
"We did not end up staying at this property because the host cancelled on us the day before. He reached out 2 months prior to tell us his pool would not be available and offered us a 20% refund. But he never provided it and did not communicate about this again. When we followed up about it, he cancelled the whole stay and tried to get us to change properties last minute. This seemed very strange so we didn’t agree. We did eventually get a full refund after a LOT of back and forth but lost over...
Fully facilitated home, 7 Beds + Pool. (Pine Bush)

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (23)
"The house was a lovely and just right for our group! Host was always very prompt to answer any questions."
Kick back & relax in this peaceful, stylish place to stay with the whole family.

Luxury School House Retreat With Sauna & Pool- 1HR from NYC

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay at Hunters property. Check in and walkthrough process with the property manager was easy. The house has plenty of space, 2 TV rooms, large kitchen and sitting room and a separate dining area. We traveled with friends, our 16 year old and our 1 year toddler. There was enough activities for everyone to enjoy. The basement has a gym, pool table, ping pong and a sauna. We look forward to coming back in the summer when the pool is open. Highly recommend this space for a...
The price is AED 3,122
AED 5,371 total
includes taxes & fees
16 Apr - 17 Apr
Luxury School House Retreat With Sauna & Pool- 1HR from NYC

Modern Villa with private pond near Legoland and Delaware River.

8.0 out of 10, Very Good, (4)
"Beautiful property and big enough for 2 families to spend a weekend. Hope to return again soon"
Modern Villa with private pond near Legoland and Delaware River.

Family Fun Getaway near Cascade Lake in Warwick NY

8.0 out of 10, Very Good, (8)
"The exterior of the home is completely run down. Nothing like the pictures. The interior bedding and furniture is a different set up then depicted. The rugs and carpets are stained and dirty. This did not meet our standards. We would not recommend it to anyone. We left a day early."
Family Fun Getaway near Cascade Lake in Warwick NY

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Big, spacious and clean. The area is calm and shops are within 5 min driving distance"
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Retreat w/ Pool, Hot Tub & Game Room

Perfect home for a dream retreat + POOL

6.0 out of 10, (2)
"To begin, before leaving for the trip I tried reaching out multiple times for check in information. Upon arrival, I was unable to check into place to stay. I tried multiple times contacting host, as well as support trying to contact the host, with NO answer. This left me to find another place to stay with short notice because we waited for 2+ hours for a reply. Unprofessional, ghosted by the host, and frustrating. This has never happened in all the years I have used Vrbo, but to summarize, do...
Perfect home for a dream retreat + POOL

Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!

6.0 out of 10, (1)
"The pictures are accurate but when you get there you see the furniture is flimsy, the cabinets and drawers fall off when you touch them and the yard is a disaster. There is so much stagnant water the mosquitos look like drones!"
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!

Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard

10.0 out of 10, Exceptional, (1)
"Loved the home didn't realize when booking it was in such a secluded spot so come prepared. House was clean minus some hair in the tubs (around drain) the closet doors attacked my sister (needs to be reinstalled and tightened) upon opening and a few draw coverings fell off. we couldn't find a broom until 10 mins before checkout (we looked all weekend )other wise the place was amazing my sister is already talking about booking in the warmer months because the yard is amazing"
Picturesque, Cozy & Fun ~ GameRoom ~ Spacious Yard

Country Manor at Millers Rock with Pool-1 Hour from NYC

Country Manor at Millers Rock with Pool-1 Hour from NYC

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Updated 3 to 4 bedroom Cape Cod

Updated 3 to 4 bedroom Cape Cod
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, (108)
"Awesome "
The price is AED 617
AED 1,030 total
includes taxes & fees
16 Apr - 17 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

9.6 out of 10, Exceptional, (5)
"Plenty of room for my family"
The price is AED 951
AED 1,213 total
includes taxes & fees
16 Apr - 17 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

9.8 out of 10, Exceptional, (59)
"2nd visit. Loved being able to use the fireplace this time!"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min 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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