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Hotel Guides > New York > Chester Hotels & Motels

Hotels in or near Chester, New York

Hotel DescriptionsMap of Hotels

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

Map of Chester Hotels

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    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 $254
    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
    Pet friendly hotel - allows pets up to 80 pounds - $30 per stay pet fee. - Nov 2015

    Most Recent HotelGuides Review
    "The hotel room was clean, and the staff was friendly and welcoming to our dogs.2017-07-04"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 224 reviews  Read Recent Reviews

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

    From $850
    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:  5.0 of 5 stars
    Based on 172 reviews  Read Recent Reviews

  • 4.1 miles Comfort Inn & Suites Goshen
    20 Hatfield Lane, Goshen, NY 10924
    4.1 miles from Chester
    From $171
    Enter Dates
    Comfort Inn & Suites Goshen

    Check In15 00
    Check Out11 00

    Rated Average
    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 Review
    "The hotel was clean, and the employees were sweet. The AC was loud, and the cool air didn't stay on long. The room was nice otherwise. The continental breakfast was just enough, and the coffee was terrific. Good place for a short stay.2018-07-24"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 63 reviews  Read Recent Reviews

  • 4.1 miles Sleep Inn & Suites Monroe
    1 Sleep Way, Monroe, NY 10950
    4.1 miles from Chester
    From $164
    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 Review
    "I had a great hotel stay.2018-05-06"


    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 17 reviews  Read Recent Reviews

  • 7 miles Holiday Inn Middletown
    68 Crystal Run Road, Middletown, NY 10941
    7 miles from Chester
    From $110
    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 Review
    "The hotel room was big, and I slept well. Nice check-in clerk. Park on the side so you can load from the side door.2017-06-28"


    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 193 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites by Wyndham Middletown
    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $108
    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
    Microwave and refrigerator in every room
    Free continental breakfast
    Free WiFi
    Free parking - truck parking
    Pet friendly hotel - allows pets up to 45 pounds - $20 per night fee for each pet. - Nov 2015

    Most Recent HotelGuides Review
    "I stayed with a handicapped friend and her dog. The staff was efficient and accommodating. I recommend this hotel.2017-01-10"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 806 reviews  Read Recent Reviews

  • 8 miles Courtyard by Marriott Hotel Middletown
    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $254
    Enter Dates
    Courtyard by Marriott Hotel Middletown

    Check In1500
    Check Out1200

    Rated 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:  4.0 of 5 stars
    Based on 318 reviews  Read Recent Reviews

  • 8 miles Hampton Inn Middletown
    20 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $149
    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 - no pet fee. - Nov 2015

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 705 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown
    4939 Route 17M, New Hampton, NY 10958
    8 miles from Chester
    From $132
    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 Review
    "Not a fancy motel, but it was clean and the beds and pillows were comfortable. Minimal lighting in the room. The exterior looked freshly painted, and I liked the warm colors. The staff accommodated our request for a late checkout. Breakfast was sparse, but got us through until lunch time. Very acceptable for a short stay.2015-08-10"


    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 186 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn Central Valley
    139 Route 32, Central Valley, NY 10917
    8 miles from Chester
    From $131
    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 Review
    "The motel was affordable and met our needs nicely. The room was clean, the bed was comfortable, and the wireless Internet worked well. We had no complaints.2016-11-18"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 303 reviews  Read Recent Reviews

  • 9 miles Home2 Suites by Hilton Middletown
    600 NY 211 East, Middletown, NY 10941
    9 miles from Chester
    From $190
    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 - $95 per stay fee for each pet. - Jan 2017

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 186 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel Middletown
    563 NY 211, Middletown, NY 10940
    9 miles from Chester
    From $79
    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 - $15 per night fee for each pet. - Nov 2015

    Most Recent HotelGuides Review
    "The room was clean, but pretty bare-bones. Only had one wastebasket and one roll of toilet paper. The hotel clerk was inefficient, slow to respond, and unprofessional. Think twice about staying here.2015-08-18"


    TripAdvisor Traveler Rating:  2.5 of 5 stars
    Based on 360 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites Middletown
    3491 Route 6, Middletown, NY 10940
    9 miles from Chester
    From $121
    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 53 reviews  Read Recent Reviews

  • 10 miles SingleThread Farm Inn Healdsburg
    131 North Street, Healdsburg, CA 95448
    10 miles from Chester
    From $1000
    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 39 reviews  Read Recent Reviews

  • 10 miles Super 8 Hotel Montgomery
    207 Montgomery Road, Montgomery, NY 12549
    10 miles from Chester
    From $73
    Enter Dates
    Super 8 Hotel Montgomery

    Check In1500
    Check Out1100

    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 - $10 per night fee for each pet. - Mar 2017

    Most Recent HotelGuides Review
    "The hotel was clean and easy to access, and the staff was friendly.2018-07-12"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 282 reviews  Read Recent Reviews

  • 11 miles Holiday Inn Express Hotel & Suites Montgomery
    491 Goodwill Road, Montgomery, NY 12549
    11 miles from Chester
    From $135
    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 Review
    "Clean room with comfortable beds. The hotel staff was friendly.2017-11-05"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 63 reviews  Read Recent Reviews

  • 13 miles Homewood Suites by Hilton New Windsor
    180 Breunig Road, New Windsor, NY 12553
    13 miles from Chester
    From $219
    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 Review
    "Convenient to stores and restaurants. The hotel room was comfortable, and the staff was accommodating.2017-03-18"
    More >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 786 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 Review
    "Good hotel near everything I needed. I was happy with the cleanliness of the room and the service.2017-11-27"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 660 reviews  Read Recent Reviews

  • 14 miles Econo Lodge New Windsor
    310 Windsor Highway, New Windsor, NY 12550
    14 miles from Chester
    From $91
    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
    2 floors, 40 rooms - no elevator
    No swimming pool
    Free continental breakfast
    Free WiFi
    Free parking
    Pet friendly hotel - allows up to 2 pets per room - $10 per night fee for each pet. - Aug 2015

    Most Recent HotelGuides Review
    "The hotel room was fine, and the staff was first-rate. No negatives. This is a perfectly good choice.2016-10-18"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 100 reviews  Read Recent Reviews

  • 14 miles Courtyard by Marriott Hotel Newburgh
    4 Governor Drive, Newburgh, NY 12550
    14 miles from Chester
    From $127
    Enter Dates
    Courtyard by Marriott Hotel Newburgh

    Check In1500
    Check Out1200

    Rated High
    Upper-midscale, smoke-free hotel 5 miles from Stewart Airport
    3 floors, 78 rooms and suites - elevator
    Free shuttle to Stewart Airport
    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. - Feb 2015

    Most Recent HotelGuides Review
    "Good hotel staff. Great experience.2016-10-27"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 189 reviews  Read Recent Reviews

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Chester Info

Pet Friendly Hotels in or near Chester

Chester Group Hotel Rates

Map of Chester NY Hotels


Nearby Attractions


Hotels near Mt Peter Ski Area
   8 miles south
Hotels near Woodbury Common Premium Outlets
   8 miles east
Hotels near Harriman State Park
   12 miles SE
Hotels near Newburgh Airport - SWF
   13 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 National Winter Activity Center
   16 miles SW
Hotels near Mountain Creek
   17 miles SW
Hotels near Montrose VA Medical Center - Montrose NY
   20 miles SE
Hotels near Fishkill Correctional Facility
   20 miles NE
Hotels near Ramapo College
   20 miles south
Hotels near Jefferson Valley Mall
   24 miles east
Hotels near Palisades Center Mall
   25 miles SE
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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
New Hampton NY Hotels
   8 miles NW
Warwick NY Hotels
   9 miles SW
Scotchtown NY Hotels
   9 miles NW
Greenwood Lake NY Hotels
   10 miles south
Middletown NY Hotels
   10 miles NW
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
Fort Montgomery NY Hotels
   15 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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