Book Villas in Chester, NY
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Villas in Chester

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Chester NY
This villa features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden is also provided.

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Monroe NY
This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.

Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC
Harriman NY
A hot tub is featured at this villa, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.

Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake
Middletown NY
This villa features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A sauna and a garden are also provided.

Luxury School House Retreat With Pool & Sauna - 1HR from NYC
New Hampton NY
$1,142 nightly
The price is $1,349 total per night
$1,349 total
Jun 9 - Jun 10
Total with taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free villa. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.

Group Retreat w. Backyard, BBQ, Gym, Games & More!
Stony Point NY
This villa features a gym and a hot tub. Families will appreciate the arcade/game room and barbecue grills. A garden and laundry facilities are also provided.

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Monroe NY
A hot tub is featured at this villa, along with laundry facilities and barbecue grills.

Modern Villa with private pond near Legoland and Delaware River.
Port Jervis NY
This villa features laundry facilities.

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe
Monroe NY
This villa includes a garden and laundry facilities.

11BR Retreat w Pool & Game Room
Chester NY
$4,487 nightly
The price is $5,076 total per night
$5,076 total
Jul 1 - Jul 2
Total with taxes and fees
This villa features an outdoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. Barbecue grills are provided for your convenience.
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.
Top hotels in Chester

DoubleTree by Hilton Hotel Nanuet
425 E Route 59 Nanuet NY
$130 nightly
The price is $152 total per night from Jun 21 to Jun 22
$152 total
Jun 21 - Jun 22
Total with taxes and fees
9/10 Wonderful! (1,147 reviews)
Chester Villas essential information
Accommodation | 17 Villas |
|---|---|
Lowest Price | $107 |
Highest Price | $5,076 |
Popular accommodation | Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC, Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake, Spacious Retreat w/ Pool, Hot Tub & Game Room, Luxury School House Retreat With Pool & Sauna - 1HR from NYC, Group Retreat w. Backyard, BBQ, Gym, Games & More!, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY., Modern Villa with private pond near Legoland and Delaware River. , Charming 3-bedroom villa with WiFi, AC in fabulous Monroe, 11BR Retreat w Pool & Game Room, Marvelous 7-bedroom villa with AC in charming Cornwall |
More ways to wander Chester
Explore More Ways to Travel with Travelocity
- Hotels near Applewood Winery
- Hotels near Goshen Historic Track
- Hotels near Ananda Ashram
- Hotels near The Rock Sports Complex
- Country Houses in Hunter
- Hotels with Pools in Blooming Grove
- Hotels with Hot Tubs in Blooming Grove
- Blooming Grove Hotels
- Hotels near Monroe Federal Plaza Shopping Center
- Beach Resorts & in Orange County
- Hotels with Pools in Orange County
- Pet Friendly Hotels in Orange County
- Cabins in Orange County
- Resorts in Orange County
- Florida Hotels
- Hotels near Museum Village
- Hotels near Castle Fun Center
- Hotels near The Golf Club at Mansion Ridge
- Hotels near Harness Racing Museum and Hall of Fame
- Hotels with Pools in Washingtonville
- Washingtonville Hotels
- Apartments in Sugar Loaf
- B&B in Sugar Loaf
- Chalets in Sugar Loaf
- Condos in Sugar Loaf
- Sugar Loaf Hotels
- Inns in Sugar Loaf
- Vacation Homes in Sugar Loaf
- Rv Parks in Sugar Loaf
- Motels in Walton Park
- 4 Star Hotels in Goshen
- Farmstay in Goshen
- B&B in Goshen
- Cabins in Goshen
- Chalets in Goshen
- Condos in Goshen
- Cottages in Goshen
- Extended Stay Hotels in Goshen
- Guest Houses in Goshen
- Casino Resorts & in Goshen
- Convention Center Hotels in Goshen
- Kid Friendly Hotels in Goshen
- Gay Friendly Hotels in Goshen
- Hotels with Pools in Goshen
- Hotels with Shopping in Goshen
- Spa Resorts & in Goshen
- Hotel Wedding Venues Hotels in Goshen
- Goshen Hotels
- Inns in Goshen
- Motels in Goshen
- Rv Parks in Goshen
- Resorts in Goshen
- Hotels near LEGOLAND® New York
- Hotels near Arrow Park Lake and Lodge
- Condos in Jones Beach Island
- Extended Stay Hotels in Jones Beach Island
- 5 Star Hotels in Monroe
- B&B in Monroe
- Chalets in Monroe
- Extended Stay Hotels in Monroe
- Guest Houses in Monroe
- Beach Resorts & in Monroe
- Cheap Hotels in Monroe
- Pet Friendly Hotels in Monroe
- Romantic Getaways & Hotels in Monroe
- Winery Hotels in Monroe
- Monroe Hotels
- Inns in Monroe
- Motels in Monroe
- Vacation Homes in Monroe
- Resorts in Monroe
- Manhattan Hotels
- Campbell Hall Hotels
- New York Hotels
- Condos in City Island
- Hostels in City Island
- Town Houses in City Island







