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Hotels > US Hotels > Hotels in New York > Chester Hotels & Motels

Hotels and Motels in or near Chester, NY


Chester is in southern New York, 40 miles southwest of Poughkeepsie and 45 miles north of Paterson, New Jersey.

Map of Chester, NY Hotels and Motels
 
 Rates shown below are averages. Use Search above to see rates for your dates.
  • Holiday Inn Express & Suites Chester

    2 Bryle Place, Chester, NY 10918

    Enter Dates
    Holiday Inn Express & Suites Chester

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-midscale, smoke-free hotel
    • 5 miles southeast of Woodbury Common Outlet Mall
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Jan 2020
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 255 reviews  Read Recent Reviews

  • Glenmere Mansion Chester

    634 Pine Hill Road, Chester, NY 10918

    Enter Dates
    Glenmere Mansion Chester

    Check In15 00
    Check Out11 00

    Rated Very High
    • Luxury, smoke-free bed and breakfast inn
    • Located on 150-acre estate
    • 3 floors, 18 rooms - elevator
    • Heated outdoor swimming pool open in summer
    • Fitness center
    • 2 restaurants
    • Full-service spa
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Nov 2015
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 231 reviews  Read Recent Reviews

  • 2.5 miles Legoland Hotel Goshen

    1 Legoland Blvd, Goshen, NY 10924
    2.5 miles to Chester

    Enter Dates
    Legoland Hotel Goshen

    Check In16 00
    Check Out11 00

    Rated Average
    • Upscale, smoke-free, full-service hotel
    • Next to Legoland New York
    • 4 floors, 250 rooms and suites
    • Outdoor swimming pool open in summer
    • Exercise room
    • Restaurant - lounge - cafe
    • Free hot breakfast buffet
  • Not pet friendly - no pets allowed. - May 2022
  • Note: This hotel charges a resort fee of $30 per night - includes parking and WiFi.
  • TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 37 reviews  Read Recent Reviews

  • 4.1 miles Sleep Inn & Suites Monroe

    1 Sleep Way, Monroe, NY 10950
    4.1 miles to Chester

    Enter Dates
    Sleep Inn & Suites Monroe

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free hotel
    • 10 miles from Schunnemunk State Park
    • 3 floors, 82 rooms and suites - elevator
    • No swimming pool
    • Exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Mar 2022
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 89 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites by Wyndham Middletown

    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles to Chester

    Enter Dates
    Microtel Inn & Suites by Wyndham Middletown

    Check In1500
    Check Out1200

    Rated Average
    • Cheap, smoke-free hotel
    • Near Galleria at Crystal Run Mall
    • 3 floors, 80 rooms and suites - elevator
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 913 reviews  Read Recent Reviews

  • 8 miles Courtyard by Marriott Hotel Middletown

    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles to Chester

    Enter Dates
    Courtyard by Marriott Hotel Middletown

    Check In1500
    Check Out1200

    Rated High
    • Upscale, smoke-free hotel
    • Near Galleria at Crystal Run
    • 4 floors, 134 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Restaurant - lounge
    • Restaurant open for breakfast and dinner only
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Nov 2015
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 368 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Middletown

    20 Crystal Run Crossing, Middletown, NY 10941
    8 miles to Chester

    Enter Dates
    Hampton Inn Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-midscale, smoke-free hotel
    • 18 miles from Woodbury Common Outlets
    • 4 floors, 127 rooms and suites
    • Heated outdoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 838 reviews  Read Recent Reviews

  • 8 miles Holiday Inn Express & Suites Middletown - I-84, Exit 19

    20 Med Parc Road, I-84, Exit 19, Middletown, NY 10940
    8 miles to Chester

    Enter Dates
    Holiday Inn Express & Suites Middletown - I-84, Exit 19

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-midscale, smoke-free, interstate hotel
    • 4 floors, 93 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 64 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown

    4939 Route 17M, New Hampton, NY 10958
    8 miles to Chester

    Enter Dates
    Days Inn Middletown

    Check In1500
    Check Out1100

    Rated Average
    • Cheap, smoke-free motel
    • 4 miles southwest of Galleria at Crystal Run Mall
    • Outdoor swimming pool open in summer
    • Free continental breakfast
    • Free WiFi
    • Free parking - limited truck parking
  • Not pet friendly - no pets allowed. - Feb 2021
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 219 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Central Valley

    60 Centre Drive, Central Valley, NY 10917
    8 miles to Chester

    Enter Dates
    Hampton Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-midscale hotel near Woodbury Common Outlet Mall
    • 3 floors, 136 rooms and suites - elevator
    • Some smoking rooms
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Feb 2019
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1023 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn Central Valley

    139 Route 32, Central Valley, NY 10917
    8 miles to Chester

    Enter Dates
    Americas Best Value Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated Average
    • Cheap, smoke-free motel
    • Near Woodbury Common Outlet Mall
    • 2 floors, 51 rooms - no elevator
    • No swimming pool
    • Microwave and refrigerator in every room
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
  • Not pet friendly - no pets allowed. - Oct 2020
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 360 reviews  Read Recent Reviews

  • 9 miles Home2 Suites by Hilton Middletown

    600 NY 211 East, Middletown, NY 10941
    9 miles to Chester

    Enter Dates
    Home2 Suites by Hilton Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-midscale, smoke-free, all-suite, extended-stay hotel
    • Near Galleria at Crystal Run
    • 4 floors, 95 studio and 1-bedroom suites
    • Indoor swimming pool - exercise room
    • Kitchen in every suite
    • Free continental breakfast
    • Free WiFi
    • Free parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 353 reviews  Read Recent Reviews

  • 9 miles La Quinta Inn & Suites Middletown

    551 NY 211, Middletown, NY 10941
    9 miles to Chester

    Enter Dates
    La Quinta Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free hotel
    • 6 miles from Hall of Fame of the Trotters
    • 19 miles from Stewart Airport
    • 4 floors, 87 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking - truck parking
  • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 31 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel Middletown

    563 NY 211, Middletown, NY 10940
    9 miles to Chester

    Enter Dates
    Super 8 Hotel Middletown

    Check In1500
    Check Out1100

    Rated Very Low – Not Recommended
    • Cheap hotel near Galleria at Crystal Run Mall
    • Some smoking rooms
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
  • Pet friendly hotel More >
  • Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  2.5 of 5 stars
    Based on 406 reviews  Read Recent Reviews

  • 9 miles Residence Inn by Marriott Middletown

    57 Tower Drive, Middletown, NY 10941
    9 miles to Chester

    Enter Dates
    Residence Inn by Marriott Middletown

    Check In1500
    Check Out1200

    Rated Very High
    • Upscale, smoke-free, all-suite, extended-stay hotel
    • Near NY 17, Exit 120
    • 1 mile from Galleria at Crystal Run Mall
    • 4 floors, 125 studio to 2-bedroom suites
    • Heated indoor swimming pool - exercise room
    • Kitchen in every suite
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - Aug 2020
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 43 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites Middletown

    3491 Route 6, Middletown, NY 10940
    9 miles to Chester

    Enter Dates
    Sleep Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free hotel near US 6 at I-84
    • 4 floors, 108 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
  • Not pet friendly - no pets allowed. - April 2020
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 111 reviews  Read Recent Reviews

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Chester Info

Chester Group Hotel Rates

Hotels near Me

Nearby Attractions


Hotels near Frozen Ropes   1.1 miles south
Hotels near Legoland New York   2.5 miles NW
Hotels near Brotherhood Winery   7 miles NE
Hotels near West Hills Country Club   7 miles NW
Hotels near Orange Regional Medical Center   7 miles NW
Hotels near Villa Venezia   8 miles NW
Hotels near Mt Peter Ski Area   8 miles south
Hotels near New York Renaissance Faire   8 miles south
Hotels near Woodbury Common Premium Outlets   8 miles east
Hotels near Falkirk Estate and Country Club   9 miles east
Hotels near Warwick Winery   10 miles SW
Hotels near Warwick Drive-In Theater   10 miles SW
Hotels near Sterling Forest State Park   11 miles south
Hotels near Storm King Art Center   12 miles east
Hotels near Harriman State Park   12 miles SE

Nearby Cities


Goshen NY Hotels   3.9 miles NW
Monroe NY Hotels   4.9 miles SE
Washingtonville NY Hotels   7 miles NE
Warwick NY Hotels   9 miles SW
Greenwood Lake NY Hotels   10 miles south
Middletown NY Hotels   10 miles NW
Tuxedo Park NY Hotels   11 miles south
Montgomery NY Hotels   12 miles north
Cornwall NY Hotels   13 miles NE
Walden NY Hotels   14 miles north
New Windsor NY Hotels   15 miles NE
Orange Lake NY Hotels   15 miles NE
Newburgh NY Hotels   17 miles NE
West Milford NJ Hotels   17 miles south
Cold Spring NY Hotels   17 miles east
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How Do We Order Hotels?

On place pages like this, we order hotels from lowest cost to highest – except we list low-rated hotels at the bottom of the page.

Most of our competitors order these same hotels in other ways that make them more money.
How Do We Define Motel?

To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.

At hotels, on the other hand, you can enter your room only through a hall inside the building.
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Hotel Booking Tips
  1. Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. +Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas?
  2. Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. +Often you cannot – because some hotels' profit strategy is to get paid more than once for the same room for the same night.
  3. Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty?
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  4. When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
  5. The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.



Chester Hotels, Motels, Lodging, and Accommodations – Chester, New York NY, USA

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