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Hotel Guides > New York > Chester Hotels & Motels

Hotels in or near Chester, New York

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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



 

    Hotels in or near Chester


  • Holiday Inn Express Hotel & Suites
    2 Bryle Place, Chester, NY 10918

    From $136
    See Rates
    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 front desk clerks were extremely helpful and friendly. I was quite impressed with the attention to detail and the quality of service. I'll definitely recommend this hotel to friends.2016-01-08"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 197 reviews  Read Recent Reviews

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

    From $775
    See Rates
    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
    Warning: Note: This hotel does not allow children under 18 years of age.
    - Nov 2015

    TripAdvisor Traveler Rating:  5.0 of 5 stars
    Based on 130 reviews  Read Recent Reviews

  • 4.1 miles Comfort Inn & Suites
    20 Hatfield Lane, Goshen, NY 10924
    4.1 miles from Chester
    From $180
    See Rates
    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 room was clean, but the shower had terrible water pressure. I complained to the hotel clerk, but no one could fix the problem. I was also disappointed that the coffee maker didn't work. Look elsewhere.2016-02-19"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 25 reviews  Read Recent Reviews

  • 7 miles Hampton Inn
    20 Crystal Run Crossing, Middletown, NY 10941
    7 miles from Chester
    From $152
    See Rates
    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 567 reviews  Read Recent Reviews

  • 8 miles Holiday Inn
    68 Crystal Run Road, Middletown, NY 10941
    8 miles from Chester
    From $152
    See Rates
    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
    "Decent room - housekeeping staff didn't speak English well; I asked for an extra blanket and got a sheet - front desk clerks were extremely friendly and helpful - nice pool area - restaurant had lousy food and grumpy servers.2009-03-01"
    More >

    TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 164 reviews  Read Recent Reviews

  • 8 miles Microtel Inn & Suites
    19 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $80
    See Rates
    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 624 reviews  Read Recent Reviews

  • 8 miles Courtyard Hotel
    24 Crystal Run Crossing, Middletown, NY 10941
    8 miles from Chester
    From $144
    See Rates
    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 262 reviews  Read Recent Reviews

  • 8 miles Days Inn Middletown
    4939 Route 17M, New Hampton, NY 10958
    8 miles from Chester
    From $102
    See Rates
    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 153 reviews  Read Recent Reviews

  • 8 miles Americas Best Value Inn
    139 Route 32, Central Valley, NY 10917
    8 miles from Chester
    From $78
    See Rates
    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 248 reviews  Read Recent Reviews

  • 9 miles Home2 Suites
    600 NY 211 East, Middletown, NY 10941
    9 miles from Chester
    From $142
    See Rates
    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:  5.0 of 5 stars
    Based on 12 reviews  Read Recent Reviews

  • 9 miles Super 8 Hotel
    563 NY 211, Middletown, NY 10940
    9 miles from Chester
    From $58
    See Rates
    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 282 reviews  Read Recent Reviews

  • 9 miles Sleep Inn & Suites 3491 Route 6, Middletown, NY 10940
    9 miles from Chester
    From $157
    See Rates
    Sleep Inn & Suites Middletown

    Check In14 00
    Check Out11 00

    Rated Average



  • 10 miles Super 8 Hotel
    207 Montgomery Road, Montgomery, NY 12549
    10 miles from Chester
    From $51
    See Rates
    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 209 reviews  Read Recent Reviews

  • 11 miles Holiday Inn Express Hotel & Suites
    491 Goodwill Road, Montgomery, NY 12549
    11 miles from Chester
    From $124
    See Rates
    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 41 reviews  Read Recent Reviews

  • 13 miles Homewood Suites
    180 Breunig Road, New Windsor, NY 12553
    13 miles from Chester
    From $133
    See Rates
    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 589 reviews  Read Recent Reviews

  • 14 miles Days Inn Stewart Airport
    915 Union Avenue, New Windsor, NY 12553
    14 miles from Chester
    From $119
    See Rates
    Days Inn Stewart Airport New Windsor

    Check In1500
    Check Out1100

    Rated Average
    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 room was a bit small, but it was clean and the staff was friendly. Beautiful view of the water on the front side. A good option.2016-11-08"
    More >

    TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 434 reviews  Read Recent Reviews

  • 14 miles Econo Lodge
    310 Windsor Highway, New Windsor, NY 12550
    14 miles from Chester
    From $77
    See Rates
    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 83 reviews  Read Recent Reviews

  • 14 miles Courtyard Hotel
    4 Governor Drive, Newburgh, NY 12550
    14 miles from Chester
    From $178
    See Rates
    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 164 reviews  Read Recent Reviews

  • 14 miles Four Points Hotel
    5 Lakeside Road, Newburgh, NY 12550
    14 miles from Chester
    From $85
    See Rates
    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 74 reviews  Read Recent Reviews

  • 14 miles Howard Johnson Inn
    95 NY 17K, Newburgh, NY 12550
    14 miles from Chester
    From $62
    See Rates
    Howard Johnson Inn Newburgh

    Check In1500
    Check Out1100

    Rated Low – Not Recommended
    Cheap, smoke-free hotel near I-84 and I-87 Convenient to West Point and US Military Academy
    4 miles from Stewart Airport
    2 floors, 74 rooms - no elevator
    No swimming pool
    Restaurant
    Restaurant open for lunch and dinner only
    Free continental breakfast
    Free Internet in room
    Free parking - truck parking
    Not pet-friendly - no pets allowed. - Feb 2017

    Most Recent HotelGuides Review
    "The room was quiet. The hallways smelled bad. Nice front desk clerks. There was a lot of swearing and threatening words at breakfast, which upset my daughter. Find another hotel.2015-07-14"
    More >

    TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 438 reviews  Read Recent Reviews

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Map of Chester NY Hotels


Hotels near
Nearby Attractions


Hotels near Woodbury Common Premium Outlets
   8 miles east
spacer Hotels near Newburgh Airport - SWF
   13 miles NE
spacer Hotels near Stewart Air National Guard Base
   14 miles NE
spacer Hotels near Michie Stadium
   16 miles east
spacer Hotels near US Military Academy
   16 miles east
spacer Hotels near USMA - US Military Academy
   16 miles east
spacer Hotels near Otisville Federal Prison
   16 miles NW
spacer Hotels near Hidden Valley
   16 miles SW
spacer Hotels near Mount Saint Mary College
   17 miles NE
spacer Hotels near Mountain Creek
   17 miles SW
spacer Hotels near Paramount Theater
   19 miles east
spacer Hotels near Montrose VA Medical Center
   20 miles SE
spacer Hotels near Fishkill Correctional Facility
   20 miles NE
spacer Hotels near Ramapo College
   20 miles south
spacer Hotels near Castle Point VA Medical Center
   21 miles NE
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Chester Hotels, Motels, Lodging, and Accommodations – Chester, New York NY, USA



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