Chestertown Hotels

Search

Search nearby for tonight

Deals Chestertown

See hotels on a map
See hotels on a map (Chestertown) - GPS: 39.2089004516602, -76.0669021606445
Hotel Pictures: Driftwood Inn, Chestertown
2.7 /5
Poor
Score from 71 reviews
Motel
  • 609 Washington Avenue MD 21620 Chestertown - View on map

Coffee is provided in the lobby and vending machines with drinks are available ... 5 miles away from the Driftwood.

  • Features of Driftwood Inn
  • Free parking
  • Soundproof rooms
  • Heating
  • Daily housekeeping
  • Budget-friendly travel
Queen Room
from 69,0 US$
King Room
Double Room with Two Double Beds
+

Approximate price - Price per room/night

TODAY
12%
OFF
Hotel Pictures: Holiday Inn Express Hotel & Suites Chestertown, Chestertown
4.3 /5
Fabulous
Score from 109 reviews
Hotel

Free Wi-Fi is available throughout the hotel ... Chestertown centre is full of boutique shops and restaurants and is 5 minutes’ drive away.

  • Features of Holiday Inn Express Hotel & Suites Chestertown
  • Casino
  • Library
  • Heating
  • Free WiFi
  • Countryside
  • Budget-friendly travel
Room Selected at Check-In
from 91,0 US$
King Room
Queen Room with Two Queen Beds
Queen Suite
King Suite with Sofa Bed
King Room - Mobility Access/Hearing Accessible
Twin Room - Mobility Access
from 87,0 US$
Two-Bedroom Suite - Mobility Accessible Tub
Suite with Mobility Accessible Tub - Non-Smoking
View all rooms Holiday Inn Express Hotel & Suites Chestertown

Approximate price - Price per room/night

TODAY
37%
OFF
Hotel Pictures: Brampton Bed and Breakfast Inn, Chestertown
4.5 /5
Fabulous
Score from 10 reviews
Bed and Breakfast
  • 25227 Chestertown Road MD 21620 Chestertown - View on map

This 19th century estate is located on Maryland’s Eastern Shore and features lush gardens, outdoor seating, and a large wrap-around terrace with ceiling fans ... The Brampton B&B is 5 minutes’ drive from Washington College.

  • Features of Brampton Bed and Breakfast Inn
  • WiFi
  • On-site parking
  • Street parking
  • Electric vehicle charging station
    King Room - Disability Access
    Superior King Room
    from 313,0 US$
    Deluxe Queen Room
    King Suite
    King Room with Garden View
    Deluxe King Suite
    King Room
    from 219,0 US$
    Queen Room with Garden View
    from 274,0 US$
    View all rooms Brampton Bed and Breakfast Inn

    Approximate price - Price per room/night

    TODAY
    11%
    OFF
    Hotel Pictures: Lodging at The Imperial, Chestertown
    Hotel

    Boasting a concierge service, this property also provides guests with a terrace ... Guest rooms at Lodging at The Imperial are equipped with a seating area, a flat-screen TV with cable channels and a private bathroom with a hair dryer and a bath.

    • Features of Lodging at The Imperial
    • Bar
    • Internet services
    • Air conditioning
    • Daily housekeeping
      Deluxe Double Room (2 Adults + 1 Child)
      from 261,0 US$
      Deluxe Double Room (2 Adults + 1 Child)
      Deluxe Apartment
      from 204,0 US$
      +

      Approximate price - Price per room/night

      Hotel Pictures: Driftwood Inn, Chestertown
      2.7 /5
      Poor
      Score from 71 reviews
      Motel
      ( Chestertown: 1.56 km)

      Coffee is provided in the lobby and vending machines with drinks are available ... 5 miles away from the Driftwood.

      • Features of Driftwood Inn
      • Free parking
      • Soundproof rooms
      • Heating
      • Daily housekeeping
      • Budget-friendly travel
      Queen Room
      from 69,0 US$
      King Room
      Double Room with Two Double Beds
      +

      Approximate price - Price per room/night

      Hotel Pictures: Holiday Inn Express Hotel & Suites Chestertown, Chestertown
      4.3 /5
      Fabulous
      Score from 109 reviews
      Hotel
      ( Chestertown: 2.12 km)

      Free Wi-Fi is available throughout the hotel ... Chestertown centre is full of boutique shops and restaurants and is 5 minutes’ drive away.

      • Features of Holiday Inn Express Hotel & Suites Chestertown
      • Casino
      • Library
      • Heating
      • Free WiFi
      • Countryside
      • Budget-friendly travel
      Room Selected at Check-In
      from 91,0 US$
      King Room
      Queen Room with Two Queen Beds
      Queen Suite
      King Suite with Sofa Bed
      King Room - Mobility Access/Hearing Accessible
      Twin Room - Mobility Access
      from 87,0 US$
      Two-Bedroom Suite - Mobility Accessible Tub
      Suite with Mobility Accessible Tub - Non-Smoking
      View all rooms Holiday Inn Express Hotel & Suites Chestertown

      Approximate price - Price per room/night

      Hotel Pictures: Brampton Bed and Breakfast Inn, Chestertown
      4.5 /5
      Fabulous
      Score from 10 reviews
      Bed and Breakfast
      ( Chestertown: 2.47 km)

      This 19th century estate is located on Maryland’s Eastern Shore and features lush gardens, outdoor seating, and a large wrap-around terrace with ceiling fans ... The Brampton B&B is 5 minutes’ drive from Washington College.

      • Features of Brampton Bed and Breakfast Inn
      • WiFi
      • On-site parking
      • Street parking
      • Electric vehicle charging station
        King Room - Disability Access
        Superior King Room
        from 313,0 US$
        Deluxe Queen Room
        King Suite
        King Room with Garden View
        Deluxe King Suite
        King Room
        from 219,0 US$
        Queen Room with Garden View
        from 274,0 US$
        View all rooms Brampton Bed and Breakfast Inn

        Approximate price - Price per room/night

        Hotel Pictures: Great Oak Manor, Great Oak Landing
        4.7 /5
        Superb
        Score from 17 reviews
        Bed and Breakfast
        ( Chestertown: 13.45 km)

        Each room is fitted with a private bathroom ... This bed and breakfast has a private beach area and free use of bicycles, kayaks, paddle-boards and golf cart is available.

        • Features of Great Oak Manor
        • Fishing
        • Canoeing
        • Private beach area
        • Private parking
          King Studio with Sofa Bed
          +
          King Suite
          Deluxe Suite with Sea View
          Deluxe King Room
          Deluxe Double Room with Balcony and Sea View - Pet-Friendly
          Deluxe Double Room with Sea View
          King Room with Garden View
          from 267,0 US$
          King Room
          Deluxe King Suite
          +
          King Room with Sea View
          from 199,0 US$
          Deluxe Double Room
          Deluxe Room
          Apartment
          +
          View all rooms Great Oak Manor

          Approximate price - Price per room/night

          Hotel Pictures: Inn at Osprey Point, Rock Hall
          4.8 /5
          Superb
          Score from 21 reviews
          Inns
          ( Chestertown: 17.55 km)

          A continental breakfast is offered at the Inn at Osprey Point ... The property offers free parking.

          • Features of Inn at Osprey Point
          • Meeting/banquet facilities
          • Babysitting/child services
          • Bridal suite
          • Airport shuttle (additional charge)
            Queen Room
            Queen Room
            from 180,0 US$
            Queen Room with Sea View
            Queen Room
            Family Room with Private Bathroom
            +
            King Room with Lake View
            King Suite with Sea View
            +
            King Room with Sea View
            King Room with Sea View
            King Room with Sea View
            King Room with Sea View
            King Room with Sea View
            Family Room with Side Sea View
            Queen Room
            Queen Room
            Twin Room with Private External Bathroom
            View all rooms Inn at Osprey Point

            Approximate price - Price per room/night

            Chestertown hotels. Reviews of Hotels Chestertown

            Welcome to Chestertown. Enter your dates and choose from over 4 properties!. Find a place to stay in Chestertown. Book the best price! Chestertown → Hotels Chestertown, Motels, Bed and breakfasts Chestertown. Cheap Hotels, Discounts, Hotel Deals and Offers • Chestertown hotels — Let ehotelsreviews.com find the perfect hotel in Chestertown for you.

            Why use ehotelsreviews.com?

            Book Now, Pay Later! With FREE cancellation on most rooms

            Unbiased reviews

            Unbiased reviews

            Our hotel reviews will help you find the best deal in the right location.

            ehotelsreviews.com provides the largest selection of hotels

            ehotelsreviews.com provides the largest selection of hotels

            ehotelsreviews.com offers the choice of over 600,000 hotels in more than 200 countries.

            Places to stay

            Places to stay

            We're more than just hotels; discover a lot more accommodation options.

            We speak your language

            We speak your language

            Website in English and 17 other languages

            See hotels on a map
            Search nearby for tonight
            Not the perfect fit? Continue search