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Hotel Guides > New York > Chester Hotels & Motels

Hotels in or near Chester, New York

Hotel DescriptionsMap of Hotels

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.



Map of Chester Hotels
 

    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

    From $136
    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
    3 floors, 80 rooms and suites - elevator
    AAA 3 Diamonds
    Heated indoor swimming pool - exercise room
    Free hot breakfast buffet
    Free WiFi
    Free parking
    Not pet friendly - no pets allowed. - Nov 2014
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 232 reviews  Read Recent Reviews

  • Glenmere Mansion Chester
    634 Pine Hill Road, Chester, NY 10918

    From $650
    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 177 reviews  Read Recent Reviews

  • 4.1 miles Comfort Inn & Suites Goshen
    20 Hatfield Lane, Goshen, NY 10924
    4.1 miles from Chester
    From $127
    Enter Dates
    Comfort Inn & Suites Goshen

    Check In15 00
    Check Out11 00

    Rated High
    Midscale, smoke-free hotel 4 miles southeast of Orange County Fair Speedway
    4 floors, 95 rooms and suites
    Outdoor swimming pool - exercise room
    Free hot breakfast buffet
    Free WiFi
    Free parking
    Not pet friendly - no pets allowed. - Nov 2015
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 70 reviews  Read Recent Reviews

  • 4.1 miles Sleep Inn & Suites Monroe
    1 Sleep Way, Monroe, NY 10950
    4.1 miles from Chester
    From $99
    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
    Free shuttle to local attractions
    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. - May 2018
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 44 reviews  Read Recent Reviews

  • 7 miles Holiday Inn Middletown
    68 Crystal Run Road, Middletown, NY 10941
    7 miles from Chester
    From $75
    Enter Dates
    Holiday Inn Middletown

    Check In15 00
    Check Out11 00

    Rated Average
    Upper-midscale hotel 18 miles northwest of Woodbury Common Outlet Mall
    2 floors, 102 rooms - elevator
    Heated indoor swimming pool
    Outdoor swimming pool - exercise room
    Restaurant - lounge
    Restaurant open for breakfast and dinner only
    Free WiFi
    Free parking - truck parking
    Not pet friendly - no pets allowed. - Nov 2015
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 204 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites by Wyndham Middletown
    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $90
    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
    3 floors, 80 rooms and suites - elevator
    No swimming pool
    Microwave and refrigerator in every room
    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 825 reviews  Read Recent Reviews

  • 8 miles Courtyard by Marriott Hotel Middletown
    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $118
    Enter Dates
    Courtyard by Marriott Hotel Middletown

    Check In1500
    Check Out1200

    Rated Very High
    Upper-midscale, 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:  4.5 of 5 stars
    Based on 332 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Middletown
    20 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $115
    Enter Dates
    Hampton Inn Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    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 735 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Central Valley
    60 Centre Drive, Central Valley, NY 10917
    8 miles from Chester
    From $163
    Enter Dates
    Hampton Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated High
    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
    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 913 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown
    4939 Route 17M, New Hampton, NY 10958
    8 miles from Chester
    From $77
    Enter Dates
    Days Inn Middletown

    Check In1500
    Check Out1100

    Rated Average
    Cheap, smoke-free motel 4 miles southwest of Galleria at Crystal Run Mall
    Single-story, 44 rooms - AAA 2 Diamonds
    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 189 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn Central Valley
    139 Route 32, Central Valley, NY 10917
    8 miles from Chester
    From $81
    Enter Dates
    Americas Best Value Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated Low – Not Recommended
    Cheap motel near Woodbury Common Outlet Mall 2 floors, 51 rooms - no elevator
    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 319 reviews  Read Recent Reviews

  • 9 miles Home2 Suites by Hilton Middletown
    600 NY 211 East, Middletown, NY 10941
    9 miles from Chester
    From $105
    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
    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 >
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 224 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel Middletown
    563 NY 211, Middletown, NY 10940
    9 miles from Chester
    From $78
    Enter Dates
    Super 8 Hotel Middletown

    Check In1500
    Check Out1100

    Rated Very Low – Not Recommended
    Cheap hotel near Galleria at Crystal Run Mall 2 floors, 82 rooms - no elevator - AAA 2 Diamonds
    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 366 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites Middletown
    3491 Route 6, Middletown, NY 10940
    9 miles from Chester
    From $112
    Enter Dates
    Sleep Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    Midscale, smoke-free hotel near US 6 at I-84 4 floors
    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. - Apr 2017
    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 63 reviews  Read Recent Reviews

  • 10 miles SingleThread Farm Inn Healdsburg
    131 North Street, Healdsburg, CA 95448
    10 miles from Chester
    From $800
    Enter Dates
    SingleThread Farm Inn Healdsburg

    Check In15 00
    Check Out11 00

    Rated Very High
    Luxury, smoke-free, downtown inn 2 floors, 5 rooms - elevator
    No swimming pool
    Restaurant
    Restaurant open for dinner only
    Free hot breakfast buffet
    Free WiFi
    Free parking - truck parking
    Not pet friendly - no pets allowed. - May 2018
    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 52 reviews  Read Recent Reviews

  • 10 miles Super 8 Hotel Montgomery
    207 Montgomery Road, Montgomery, NY 12549
    10 miles from Chester
    From $81
    Enter Dates
    Super 8 Hotel Montgomery

    Check In15 00
    Check Out11 00

    Rated Average
    Cheap hotel 8 miles northeast of Middletown 8 miles from Stewart Airport
    3 floors, 96 rooms - elevator
    No swimming pool
    Free continental breakfast
    Free WiFi
    Free parking - truck parking
    Pet friendly hotel More >
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 285 reviews  Read Recent Reviews

  • 11 miles Holiday Inn Express Hotel & Suites Montgomery
    491 Goodwill Road, Montgomery, NY 12549
    11 miles from Chester
    From $117
    Enter Dates
    Holiday Inn Express Hotel & Suites Montgomery

    Check In15 00
    Check Out11 00

    Rated High
    Midscale, smoke-free hotel near downtown Montgomery 3 floors, 81 rooms and suites - elevator
    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 2017
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 68 reviews  Read Recent Reviews

  • 13 miles Homewood Suites by Hilton New Windsor
    180 Breunig Road, New Windsor, NY 12553
    13 miles from Chester
    From $115
    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
    4 floors, 125 studio to 2-bedroom suites
    Free 24-hour shuttle to Stewart Airport
    Heated indoor swimming pool - exercise room
    Kitchen in every suite
    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 835 reviews  Read Recent Reviews

  • 14 miles Days Inn Stewart Airport New Windsor
    915 Union Avenue, New Windsor, NY 12553
    14 miles from Chester
    From $85
    Enter Dates
    Days Inn Stewart Airport New Windsor

    Check In1500
    Check Out1100

    Rated High
    Cheap hotel 3 miles from Stewart Airport 2 floors, 98 rooms - elevator
    Free shuttle to Stewart Airport
    Heated outdoor swimming pool open in summer
    Exercise room
    Free continental breakfast
    Free WiFi
    Free parking
    Park and fly costs $10 per night
    Not pet friendly - no pets allowed. - Apr 2015
    Most Recent HotelGuides Reviews Read >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 680 reviews  Read Recent Reviews

  • 14 miles Econo Lodge New Windsor
    310 Windsor Highway, New Windsor, NY 12550
    14 miles from Chester
    From $76
    Enter Dates
    Econo Lodge New Windsor

    Check In15 00
    Check Out11 00

    Rated Average
    Cheap hotel 10 miles from West Point 12 miles from Woodbury Common Premium Outlets
    2 floors, 40 rooms - no elevator
    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 104 reviews  Read Recent Reviews

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

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Chester Info

Chester Group Hotel Rates

Map of Chester NY Hotels

Nearby Attractions


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 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 Harriman State Park
   12 miles SE
Hotels near Newburgh Airport - SWF
   13 miles NE
Hotels near Stewart Air National Guard Base
   14 miles NE
Hotels near Anthony's Pier 9
   15 miles NE
Hotels near Michie Stadium
   16 miles east
Hotels near US Military Academy
   16 miles east
Hotels near USMA – U.S. Military Academy
   16 miles east
Hotels near Otisville Federal Prison
   16 miles NW
Hotels near Highlands Country Club
   17 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
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
Walden NY Hotels
   14 miles north
New Windsor NY Hotels
   15 miles NE
Orange Lake NY Hotels
   15 miles NE
Highland Falls NY Hotels
   16 miles east
West Point NY Hotels
   16 miles east
How Do We Order Hotels Below?

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

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