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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.

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

Map of Chester Hotels

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    Hotels in or near Chester

    Rates shown below are estimates. Click See Rates for actual current rates.
  • Holiday Inn Express Hotel & Suites
    2 Bryle Place, Chester, NY 10918

    From $110
    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 Internet in room
    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 206 reviews  Read Recent Reviews

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

    From $750
    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Nov 2015

    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 143 reviews  Read Recent Reviews

  • 4.1 miles Comfort Inn & Suites
    20 Hatfield Lane, Goshen, NY 10924
    4.1 miles from Chester
    From $135
    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Nov 2015

    Most Recent HotelGuides Review
    "The hotel staff was extremely friendly and helpful.2017-06-22"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 37 reviews  Read Recent Reviews

  • 7 miles Hampton Inn
    20 Crystal Run Crossing, Middletown, NY 10941
    7 miles from Chester
    From $102
    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 Internet in room
    Free parking
    Pet-friendly hotel - no pet fee. - Nov 2015

    Most Recent HotelGuides Review
    "Clean and attractive - coffee available all day in the lobby - great breakfast - wonderful stay.2008-05-01"
    More >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 615 reviews  Read Recent Reviews

  • 8 miles Holiday Inn
    68 Crystal Run Road, Middletown, NY 10941
    8 miles from Chester
    From $155
    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 Internet in room
    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"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 174 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites
    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $99
    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 Internet in room
    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 704 reviews  Read Recent Reviews

  • 8 miles Courtyard Hotel
    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $163
    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Nov 2015

    Most Recent HotelGuides Review
    "Room was comfortable and clean - breakfast was too expensive.2009-12-01"
    More >

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 279 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown
    4939 Route 17M, New Hampton, NY 10958
    8 miles from Chester
    From $144
    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 Internet in room
    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"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 171 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn
    139 Route 32, Central Valley, NY 10917
    8 miles from Chester
    From $110
    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 Internet in room
    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 263 reviews  Read Recent Reviews

  • 9 miles Home2 Suites
    600 NY 211 East, Middletown, NY 10941
    9 miles from Chester
    From $199
    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 Internet in room
    Free parking
    Pet-friendly hotel - $95 per stay fee for each pet. - Jan 2017

    TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 93 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel
    563 NY 211, Middletown, NY 10940
    9 miles from Chester
    From $96
    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 Internet in room
    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"
    More >

    TripAdvisor Traveler Rating:  2.5 of 5 stars
    Based on 327 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites
    3491 Route 6, Middletown, NY 10940
    9 miles from Chester
    From $177
    Enter Dates
    Sleep Inn & Suites Middletown

    Check In14 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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Apr 2017

    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 10 reviews  Read Recent Reviews

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

    Check In1500
    Check Out1100

    Rated Low – Not Recommended
    Cheap hotel 8 miles northeast of Middletown 8 miles from Stewart Airport
    3 floors, 96 rooms - elevator
    No swimming pool
    Free continental breakfast
    Free Internet in room
    Free parking - truck parking
    Pet-friendly hotel - $10 per night fee for each pet. - Mar 2017

    Most Recent HotelGuides Review
    "The hotel room was marginal at best. Breakfast was good, though.2015-04-23"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 239 reviews  Read Recent Reviews

  • 11 miles Holiday Inn Express Hotel & Suites
    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 Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Feb 2017

    Most Recent HotelGuides Review
    "The suite was just a large room with a bed and sofa. Entire hotel staff was friendly, courteous, and helpful.2015-02-03"


    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 47 reviews  Read Recent Reviews

  • 13 miles Homewood Suites
    180 Breunig Road, New Windsor, NY 12553
    13 miles from Chester
    From $153
    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 Internet in room
    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 678 reviews  Read Recent Reviews

  • 14 miles Days Inn Stewart Airport
    915 Union Avenue, New Windsor, NY 12553
    14 miles from Chester
    From $109
    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 Internet in room
    Free parking
    Park and fly costs $10 per night
    Not pet-friendly - no pets allowed. - Apr 2015

    Most Recent HotelGuides Review
    "The hotel was clean and a good value. I was satisfied.2017-07-09"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 546 reviews  Read Recent Reviews

  • 14 miles Econo Lodge
    310 Windsor Highway, New Windsor, NY 12550
    14 miles from Chester
    From $90
    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 Internet in room
    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 88 reviews  Read Recent Reviews

  • 14 miles Courtyard Hotel
    4 Governor Drive, Newburgh, NY 12550
    14 miles from Chester
    From $152
    Enter Dates
    Courtyard by Marriott Hotel Newburgh

    Check In1500
    Check Out1200

    Rated Average
    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 Internet in room
    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 178 reviews  Read Recent Reviews

  • 14 miles Four Points Hotel
    5 Lakeside Road, Newburgh, NY 12550
    14 miles from Chester
    From $135
    Enter Dates
    Four Points by Sheraton Hotel Newburgh

    Check In1500
    Check Out1100

    Rated Average
    Upper-midscale, smoke-free hotel 4.5 miles from Newburgh Stewart Airport
    3 floors, 124 rooms and suites - elevator
    Free shuttle to Newburgh Airport
    Outdoor swimming pool - exercise room
    Restaurant - lounge - room service
    Restaurant open for breakfast and dinner only
    Free Internet in room
    Free parking
    Not pet-friendly - no pets allowed. - Oct 2015

    Most Recent HotelGuides Review
    "The room was quiet despite the proximity of the highway and airport. It was clean and had a comfortable bed with plenty of fluffy pillows. Pleasant, easy check-in and checkout. Plenty of coffee and tea available. The restaurant was clean, and the service was speedy. Feel confident booking here.2017-02-08"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 90 reviews  Read Recent Reviews

  • 14 miles Hampton Inn & Suites 1 Crossroads Court, Newburgh, NY 12550
    14 miles from Chester
    From $152
    Enter Dates
    Hampton Inn & Suites Newburgh

    Check In15 00
    Check Out11 00

    Rated Average



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Chester Info

Pet-Friendly Chester Hotels

Map of Chester NY Hotels


Hotels near
Nearby Attractions


Hotels near Woodbury Common Premium Outlets
   8 miles east
Hotels near Newburgh Airport - SWF
   13 miles NE
Hotels near Stewart Air National Guard Base
   14 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 Hidden Valley
   16 miles SW
Hotels near Mount Saint Mary College
   17 miles NE
Hotels near Mountain Creek
   17 miles SW
Hotels near Rockland Community College
   18 miles SE
Hotels near Paramount Theater
   19 miles east
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

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Hotels in
Nearby Cities


Goshen NY Hotels
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Monroe NY Hotels
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Washingtonville NY Hotels
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Scotchtown NY Hotels
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Greenwood Lake NY Hotels
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Middletown NY Hotels
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Montgomery NY Hotels
   12 miles north
Cornwall NY Hotels
   13 miles NE
Bear Mountain NY Hotels
   14 miles east
Walden NY Hotels
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Fort Montgomery NY Hotels
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New Windsor NY Hotels
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Chester Hotels, Motels, Lodging, and Accommodations – Chester, New York NY, USA



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