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Hotels in or near Chester, New York


Hotels below are sorted by distance from Chester.

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

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Map of Chester, NY Hotels and Motels
 

Hotels in or near Chester

Rates shown below are averages. Click See Rates to see rates for your dates.
  • Holiday Inn Express Hotel & Suites Chester

    2 Bryle Place, Chester, NY 10918

    Enter Dates
    Holiday Inn Express Hotel & Suites Chester

    Check In15 00
    Check Out11 00

    Rated High
    • 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 243 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
    • 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 194 reviews  Read Recent Reviews

  • 4.1 miles Sleep Inn & Suites Monroe

    1 Sleep Way, Monroe, NY 10950
    4.1 miles

    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
    • Free shuttle to local attractions
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - May 2018
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 62 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites by Wyndham Middletown

    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles

    Enter Dates
    Microtel Inn & Suites by Wyndham Middletown

    Check In15 00
    Check Out12 00

    Rated Average
    • Cheap, smoke-free hotel
    • Near Galleria at Crystal Run Mall
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 869 reviews  Read Recent Reviews

  • 8 miles Courtyard by Marriott Hotel Middletown

    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles

    Enter Dates
    Courtyard by Marriott Hotel Middletown

    Check In1500
    Check Out1200

    Rated Very High
    • Upscale, smoke-free hotel
    • Near Galleria at Crystal Run
    • Heated indoor swimming pool - exercise room
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Nov 2015
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 357 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Middletown

    20 Crystal Run Crossing, Middletown, NY 10941
    8 miles

    Enter Dates
    Hampton Inn Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free hotel
    • 18 miles from Woodbury Common Outlets
    • Heated outdoor swimming pool - exercise 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 799 reviews  Read Recent Reviews

  • 8 miles Holiday Inn Express Hotel & Suites Middletown

    20 Med Parc Road, Middletown, NY 10940
    8 miles

    Enter Dates
    Holiday Inn Express Hotel & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free, interstate hotel
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Pet friendly hotel More >
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 12 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown

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

    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 - truck parking
    Not pet friendly - no pets allowed. - Apr 2015
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 206 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Central Valley

    60 Centre Drive, Central Valley, NY 10917
    8 miles

    Enter Dates
    Hampton Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale hotel near Woodbury Common Outlet Mall
    • Some smoking rooms
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Feb 2019
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 978 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn Central Valley

    139 Route 32, Central Valley, NY 10917
    8 miles

    Enter Dates
    Americas Best Value Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated Average
    • Cheap motel near Woodbury Common Outlet Mall
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Oct 2014
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 351 reviews  Read Recent Reviews

  • 9 miles Tru by Hilton Hotel Middletown

    41 Dunning Road, Middletown, NY 10940
    9 miles

    Enter Dates
    Tru by Hilton Hotel Middletown

    Check In15 00
    Check Out12 00

    Rated High
    • Midscale, smoke-free hotel
    • No swimming pool
    • Exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Pet friendly hotel More >
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 71 reviews  Read Recent Reviews

  • 9 miles Home2 Suites by Hilton Middletown

    600 NY 211 East, Middletown, NY 10941
    9 miles

    Enter Dates
    Home2 Suites by Hilton Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free, all-suite hotel
    • Near Galleria at Crystal Run
    • Indoor swimming pool - exercise room
    • Free continental breakfast
    • Free WiFi
    • Free parking
    Pet friendly hotel More >
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 302 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel Middletown

    563 NY 211, Middletown, NY 10940
    9 miles

    Enter Dates
    Super 8 Hotel Middletown

    Check In1500
    Check Out1100

    Rated Very Low – Not Recommended
    • Cheap hotel near Galleria at Crystal Run Mall
    • 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 379 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites Middletown
    3491 Route 6, Middletown, NY 10940
    9 miles

    Enter Dates
    Sleep Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    • Midscale, smoke-free hotel near US 6 at I-84
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - April 2020

  • 10 miles Super 8 Hotel Montgomery

    207 Montgomery Road, Montgomery, NY 12549
    10 miles

    Enter Dates
    Super 8 Hotel Montgomery

    Check In1500
    Check Out1100

    Rated Average
    • Cheap hotel 8 miles northeast of Middletown
    • 8 miles from Stewart Airport
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    Not pet friendly - no pets allowed. - Mar 2017
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 304 reviews  Read Recent Reviews

  • 11 miles Holiday Inn Express Hotel & Suites Montgomery

    491 Goodwill Road, Montgomery, NY 12549
    11 miles

    Enter Dates
    Holiday Inn Express Hotel & Suites Montgomery

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free hotel near downtown Montgomery
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Feb 2017
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 75 reviews  Read Recent Reviews

  • 13 miles Homewood Suites by Hilton New Windsor

    180 Breunig Road, New Windsor, NY 12553
    13 miles

    Enter Dates
    Homewood Suites by Hilton New Windsor

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upscale, all-suite, extended-stay hotel
    • Less than 1 mile from Stewart Airport
    • Free 24-hour shuttle to Stewart Airport
    • Heated indoor swimming pool - exercise room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking - truck parking
    Not pet friendly - no pets allowed. - Jan 2016
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 916 reviews  Read Recent Reviews

  • 14 miles Red Roof Inn & Suites New Windsor

    915 Union Avenue, New Windsor, NY 12553
    14 miles

    Enter Dates
    Red Roof Inn & Suites New Windsor

    Check In15 00
    Check Out11 00

    Rated High
    • Cheap, smoke-free, airport hotel
    • 3 miles from Stewart Airport
    • Free shuttle or hotel-paid taxi to Stewart Airport
    • Indoor swimming pool open in summer - exercise room
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    • Park and fly not allowed
    Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 737 reviews  Read Recent Reviews

  • 14 miles Econo Lodge New Windsor

    310 Windsor Highway, New Windsor, NY 12550
    14 miles

    Enter Dates
    Econo Lodge New Windsor

    Check In15 00
    Check Out11 00

    Rated Low – Not Recommended
    • Cheap hotel 10 miles from West Point
    • 12 miles from Woodbury Common Premium Outlets
    • Some smoking rooms
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking
    Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 121 reviews  Read Recent Reviews

  • 14 miles Courtyard by Marriott Hotel Newburgh

    4 Governor Drive, Newburgh, NY 12550
    14 miles

    Enter Dates
    Courtyard by Marriott Hotel Newburgh

    Check In1500
    Check Out1200

    Rated Average
    • Upscale, smoke-free hotel
    • 5 miles from Stewart Airport
    • Free shuttle to Stewart Airport
    • Heated indoor swimming pool - exercise room
    • Free WiFi
    • Free parking
    Not pet friendly - no pets allowed. - Feb 2015
    Most Recent HotelGuides Reviews Read >
    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 215 reviews  Read Recent Reviews

We can also help you find hotels in Chester, Pennsylvania and in Chester, Vermont.

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Chester Info

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Hotels near Me

Nearby Attractions


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 Crystal Run Crossing   8 miles NW
Hotels near Villa Venezia   8 miles NW
Hotels near Mt Peter Ski Area   8 miles south
Hotels near Woodbury Common Premium Outlets   8 miles east
Hotels near Falkirk Estate and Country Club   9 miles east
Hotels near Middletown High School   9 miles NW
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 Kingdom Hall of Jehovah's Witnesses   11 miles SW
Hotels near Storm King Art Center   12 miles east
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Nearby Cities


Goshen NY Hotels   3.9 miles NW
Monroe NY Hotels   4.9 miles SE
Washingtonville NY Hotels   7 miles NE
Harriman NY Hotels   8 miles SE
Central Valley NY Hotels   8 miles east
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
Bear Mountain NY Hotels   14 miles east
Walden NY Hotels   14 miles north
New Windsor NY Hotels   15 miles NE
Orange Lake NY Hotels   15 miles NE
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.
Hotel Tips

Important Hotel Tips


Chester Hotels near Me

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

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