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Chester, NY Hotels & Motels | HotelGuides.com
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Hotels > US Hotels > Hotels in New York > Chester Hotels & Motels

Hotels and Motels in or near Chester, NY


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

Map of Chester, NY Hotels and Motels
 
  • Holiday Inn Express & Suites Chester
    2 Bryle Place, Chester, NY 10918 Call Us

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    Dates
    Holiday Inn Express & Suites Chester

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 255 reviews 
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  • Glenmere Mansion Chester
    634 Pine Hill Road, Chester, NY 10918 Call Us

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    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
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 231 reviews 
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  • Legoland Hotel Goshen
    1 Legoland Blvd, Goshen, NY 10924 Call Us 2.4 miles
    2.4 miles from Chester

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    Dates
    Legoland Hotel Goshen

    Check In16 00
    Check Out11 00

    Rated Average
    • Upscale, smoke-free, full-service hotel
    • Next to Legoland New York
    • 4 floors, 250 rooms and suites
    • Outdoor swimming pool open in summer
    • Exercise room
    • Restaurant - lounge - cafe
    • Free hot breakfast buffet
    • Not pet friendly
  • Note: This hotel charges a resort fee of $30 per night - includes parking and WiFi.
  • TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 37 reviews 
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  • Sleep Inn & Suites Monroe
    1 Sleep Way, Monroe, NY 10950 Call Us 4.1 miles
    4.1 miles from Chester

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    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
    • No swimming pool
    • Exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 89 reviews 
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  • Microtel Inn & Suites by Wyndham Middletown
    19 Crystal Run Crossing, Middletown, NY 10941 Call Us 8 miles
    8 miles from Chester

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    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
    • Free continental breakfast
    • Free WiFi
    • Free parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 913 reviews 
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  • Courtyard by Marriott Hotel Middletown
    24 Crystal Run Crossing, Middletown, NY 10941 Call Us 8 miles
    8 miles from Chester

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    Dates
    Courtyard by Marriott Hotel Middletown

    Check In1500
    Check Out1100

    Rated High
    • Upscale, 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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 368 reviews 
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  • Hampton Inn Middletown
    20 Crystal Run Crossing, Middletown, NY 10941 Call Us 8 miles
    8 miles from Chester

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    Dates
    Hampton Inn Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-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 >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 838 reviews 
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  • Holiday Inn Express & Suites Middletown - I-84, Exit 19
    20 Med Parc Road, I-84, Exit 19, Middletown, NY 10940 Call Us 8 miles
    8 miles from Chester

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    Dates
    Holiday Inn Express & Suites Middletown - I-84, Exit 19

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-midscale, smoke-free, interstate hotel
    • 4 floors, 93 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 64 reviews 
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  • Days Inn Middletown
    4939 Route 17M, New Hampton, NY 10958 Call Us 8 miles
    8 miles from Chester

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    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 - limited truck parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  3.5 of 5 stars
    Based on 219 reviews 
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  • Hampton Inn Central Valley
    60 Centre Drive, Central Valley, NY 10917 Call Us 8 miles
    8 miles from Chester

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    Dates
    Hampton Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated High
    • Upper-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
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 1023 reviews 
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  • Americas Best Value Inn Central Valley
    139 Route 32, Central Valley, NY 10917 Call Us 8 miles
    8 miles from Chester

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    Dates
    Americas Best Value Inn Central Valley

    Check In15 00
    Check Out11 00

    Rated Low – Not Recommended
    • Cheap, smoke-free motel
    • Near Woodbury Common Outlet Mall
    • 2 floors, 51 rooms - no elevator
    • No swimming pool
    • Microwave and refrigerator in every room
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  3.0 of 5 stars
    Based on 360 reviews 
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  • Home2 Suites by Hilton Middletown
    600 NY 211 East, Middletown, NY 10941 Call Us 9 miles
    9 miles from Chester

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    Dates
    Home2 Suites by Hilton Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Upper-midscale, smoke-free, all-suite, extended-stay 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 353 reviews 
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  • La Quinta Inn & Suites Middletown
    551 NY 211, Middletown, NY 10941 Call Us 9 miles
    9 miles from Chester

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    Dates
    La Quinta Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated Very High
    • Midscale, smoke-free hotel
    • 6 miles from Hall of Fame of the Trotters
    • 19 miles from Stewart Airport
    • 4 floors, 87 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking - truck parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 31 reviews 
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  • Super 8 Hotel Middletown
    563 NY 211, Middletown, NY 10940 Call Us 9 miles
    9 miles from Chester

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    Dates
    Super 8 Hotel Middletown

    Check In1500
    Check Out1100

    Rated Very Low – Not Recommended
    • Cheap hotel near Galleria at Crystal Run Mall
    • Some smoking rooms
    • No swimming pool
    • Free continental breakfast
    • Free WiFi
    • Free parking - truck parking
    • Pet friendly hotel More >
  • TripAdvisor Traveler Rating:  2.5 of 5 stars
    Based on 406 reviews 
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    More Reviews

  • Residence Inn by Marriott Middletown
    57 Tower Drive, Middletown, NY 10941 Call Us 9 miles
    9 miles from Chester

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    Dates
    Residence Inn by Marriott Middletown

    Check In1500
    Check Out1200

    Rated Very High
    • Upscale, smoke-free, all-suite, extended-stay hotel
    • Near NY 17, Exit 120
    • 1 mile from Galleria at Crystal Run Mall
    • 4 floors, 125 studio to 2-bedroom suites
    • Heated indoor swimming pool - exercise room
    • Kitchen in every suite
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.5 of 5 stars
    Based on 43 reviews 
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  • Sleep Inn & Suites Middletown
    3491 Route 6, Middletown, NY 10940 Call Us 9 miles
    9 miles from Chester

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    Dates
    Sleep Inn & Suites Middletown

    Check In15 00
    Check Out11 00

    Rated High
    • Midscale, smoke-free hotel near US 6 at I-84
    • 4 floors, 108 rooms and suites
    • Heated indoor swimming pool - exercise room
    • Microwave and refrigerator in every room
    • Free hot breakfast buffet
    • Free WiFi
    • Free parking
    • Not pet friendly
  • TripAdvisor Traveler Rating:  4.0 of 5 stars
    Based on 111 reviews 
    Read Recent Reviews

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

I loved that HotelGuides helped me find a hotel. You can try to search for one yourself, but this service was so helpful. Just click on the section of the Interstate you are driving on and you see a list of hotels that actually have rooms available.

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Chester Info

Chester Group Hotel Rates

Hotels near Me

Nearby Attractions


Hotels near Frozen Ropes   1.1 miles south
Hotels near Legoland New York   2.7 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 Villa Venezia   8 miles NW
Hotels near Mt Peter Ski Area   8 miles south
Hotels near New York Renaissance Faire   8 miles south
Hotels near Woodbury Common Premium Outlets   8 miles east
Hotels near Falkirk Estate and Country Club   9 miles east
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 Storm King Art Center   12 miles east
Hotels near City Winery Hudson Valley   12 miles north

Nearby Cities


Goshen NY Hotels   3.9 miles NW
Monroe NY Hotels   4.9 miles SE
Washingtonville NY Hotels   7 miles NE
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
Newburgh NY Hotels   17 miles NE
West Milford NJ Hotels   17 miles south
Cold Spring NY Hotels   17 miles east
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.
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Hotel Booking Tips
  1. Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. +Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas?
  2. Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. +Often you cannot – because some hotels' profit strategy is to get paid more than once for the same room for the same night.
  3. Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty?
    More >
  4. When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
  5. The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.



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

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