Book Guest Houses in Chester, NY
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Top Guest Houses in Chester
Large Secluded Private Estate accommodates 18+. 12 Min. from Town of New Paltz
Pine Bush NY
This guesthouse features a water park, a garden, and barbecue grills.
Pet friendly
Free WiFi
Heritage House
579 County Route 50 New Hampton NY
This guesthouse features free self parking and WiFi in public areas. A computer station is also provided.
Parking included
Free WiFi
Infinity Mountview
6 Ekes Ct Sussex NJ
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the playground and onsite laundry facilities. Enjoy the a full-service spa and conveniences like a garden and barbecue grills.
Spa
Parking included
Charming house surrounded lakes and the fresh air of the mountains
Monroe NY
This guesthouse features a water park, a garden, and laundry facilities. Families will appreciate the playground and barbecue grills.
Pool
Pet friendly
Mary Mills Room
New Hampton NY
Book a stay at this golf guesthouse in New Hampton. Enjoy an in-room coffeemaker and air conditioning. Popular attractions LEGOLAND® New York and Soons Orchards are located nearby.
Air conditioning
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
$98 nightly
The price is $114 total per night from Jan 4 to Jan 5
$114 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Chester Guest Houses essential information
Accommodation | 6 Guest Houses |
|---|---|
Lowest Price | $85 |
Highest Price | $133 |
Popular accommodation | Large Secluded Private Estate accommodates 18+. 12 Min. from Town of New Paltz, Heritage House, Infinity Mountview, Charming house surrounded lakes and the fresh air of the mountains, Mary Mills Room, Susan Murray Room |
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