Best Chestertown Hotels

When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland. This hotel is 1.6 mi (2.6 km) from River Arts Chestertown and 5.9 mi (9.6 km) from Rolphs Wharf Marina. Be sure to enjoy recreational amenities including a fitness center and a seasonal outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, a fireplace in the lobby, and a banquet hall. A complimentary full breakfast is served on weekdays from 6:30 AM to 9:30 AM. Featured amenities include a business center, a 24-hour front desk, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 81 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include desks and microwaves, as well as phones with free local calls.

When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland. This hotel is 1.6 mi (2.6 km) from River Arts Chestertown and 5.9 mi (9.6 km) from Rolphs Wharf Marina.Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and a fireplace in the lobby. This hotel also features a banquet hall and a vending machine.A complimentary full breakfast is served on weekdays from 6:30 AM to 9:30 AM.Featured amenities include a business center, a 24-hour front desk, and laundry facilities. Free self parking is available onsite.Make yourself at home in one of the 81 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include desks and microwaves, as well as phones with free local calls.

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round. Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand.In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.During your stay you will have exclusive access to the following rooms and spaces:- Bedroom- Full bathroom- Kitchenette- Living room- Dining area- PatioAdditionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.Here's what some of our recent guests have said about their stay:"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - CarlaWe're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you. Book now to secure your spot!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.While not child friendly, we can accommodate..About customRules:There is a maximum stay of one month for Instant Bookings. For longer stays, please message the host first. Otherwise, your booking may be cancelled..The max number of guests is two people. If you are two adults traveling with a child under 5, we can accommodate but you must let us know at booking..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 12 minutes by foot from Rolling Road Park. This motel is 0.7 mi (1.1 km) from Chestertown Dog Park and 1.1 mi (1.8 km) from Historical Society of Kent County Maryland. This motel has 1 floor in 2 buildings and offers designated smoking areas. Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.

With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre. Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless internet access, gift shops/newsstands, and a picnic area. Enjoy a satisfying meal at Fairlee's serving guests of The Lodge at Great Oak Landing. Relax with a refreshing drink at one of the 3 bars/lounges. Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite. Stay in one of 29 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.

Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor. This spa bed & breakfast is 2.6 mi (4.1 km) from Waterman’s Museum and 3.3 mi (5.4 km) from Ferry Park. Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area. A complimentary local cuisine breakfast is served daily from 8:30 AM to 9:00 AM. Free self parking is available onsite. Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.