Location: Chestertown
Top Hotels in Chestertown
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Top 6 hotels in Chestertown, United States
With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Things to do in Chestertown
1. Holiday Inn Express Hotel & Suites Chestertown
Overall Ratings
4 based on 185 reviews
Welcome to the Holiday Inn Express Hotel in Chestertown, Maryland near Washington College. Our new Chestertown hotel near Washington College provides comfortable hotel rooms in Chestertown, Maryland. Our Chestertown hotel is located near several Chestertown attractions including the Hopkins Game Farm, Goose Valley Farms, Crimson Staples, Crumpton Auctions and the Waterman's Museum. Guests can further enjoy their Chestertown vacation by taking advantage of the one-of-a-kind shopping experience historical downtown Chestertown offers. Downtown Chestertown, just minutes from our hotel, houses several locally owned and operated stores. Conveniently located near the Chester River, guests of our hotel in Chestertown, Maryland, can enjoy Maryland's picturesque New England scenery while paddling or riding down the Chester River. Visitors can also take walking tours of historical Chestertown, MD, discover Chestertown's rich maritime history or take daytime or sunset sailing tours. Unlike other Chestertown hotels, the Holiday Inn Express Hotel in Chestertown, Maryland, offers comfortable rooms and is conveniently located near Washington College. During your Chestertown visit, enjoy our hotel's signature hot breakfast bar along with other amenities such as high-speed, wireless Internet access and an indoor pool. Make your reservations at our Chestertown, MD, hotel today and enjoy our excellent hotel rates.
Mrs and Mr Johnson
Reviewed By 8712BeveelyWhen u come in the morning from a walk the halls smell freshly cleaned,and the front desk staff was awesome I checked in with I believe Linda,she greeted us when we came in,helped us choose a restaurant smoothe check in And the gentleman Christian was so nice to come to our room to fix the tv,and the beds were awesome sleep so good rooms need a little update but overall great stay we will be back
2. Brampton Inn
Overall Ratings
5 based on 868 reviews
Discover an historic and award winning bed and breakfast in Chestertown, MD. Our romantic Chestertown, Maryland boutique inn is situated on 35 beautiful acres with gorgeous gardens, glorious views and scrumptious breakfasts! Unforgettable rooms and suites at our Chesapeake bed and breakfast offer spa tubs, body-jetted showers, wood burning fireplaces, robes, smart TVs, and free Wi-Fi. Treat someone special to the most romantic setting of any of Maryland's Eastern Shore inns.
"An Oasis Away from the Crowd"
Reviewed By D8354MNreneemMy husband and I have come to think of the Brampton as our second home, This beautiful piece of property has become our oasis away from the noise and stress of everyday. The beautify of the landscape and the kindness of the staff and owners and the delicious breakfast served each morning makes this more than your average vacation, but an experience to remember and cherish.
3. Comfort Inn & Suites Chestertown
Overall Ratings
4 based on 7 reviews
An overnight to visit with family
Reviewed By KAREN BWe were meeting our daughter who was performing at a conference at Washington College and our grandson for the first time. First off our key cards didn’t work to get in from the parking lot which is at the rear of the building. Had to go back three times. Everyone was complaining about this problem making it necessary to walk all the way to the front of the building. Had to do this multiple times. The beds were comfortable but one looked like it had just been remade not with fresh linens. The rug had not been vacuumed and the room needed to be dusted. The bathroom floor was disgusting and even looked like it had a blood stain on it along with so much pubic hair. There was no kleenex in both dispensers and the mirror needed to be cleaned. It was a nice quiet night though. They really need to teach their employees how to clean the the rooms properly especially with Covid.
4. Red Roof Inn & Suites Chestertown
Overall Ratings
3.5 based on 143 reviews
Red Roof Inn & Suites Chestertown is one of the best budget hotels in Chestertown, MD that is conveniently located near the crossroads of MD 213 and MD 291. We offer our guests free Wi-Fi, a guest coin laundry facility and free coffee in the lobby. Guests also have access to our designated pet area and free parking. Red Roof Inn & Suites Chestertown is a pet-friendly hotel where one well-behaved pet per room is welcome. Red Roof Inn & Suites Chestertown, Maryland is a pet-friendly, family-friendly discount hotel. This hotel is close to Washington College, Chestertown Marina, Wilmer Park, Chesapeake Farms Wildlife Habitat Tour as well as numerous historical sites and museums such as Chestertown Electric , Historical Society-Kent County, Sumner Hall, Kent County Museum, Rock Hall Marine Restoration & Heritage Center, and the Waterman’s Museum. Red Roof Inn & Suites Chestertown features interior corridors, and a guest coin laundry. All rooms at this Red Roof Inn & Suites offer free Wi-Fi, a flat screen TV, microwave, mini-fridge, in-room coffee maker, hair dryer, iron & ironing board, desk, free in-room safe and a free expanded cable package featuring HBO. Experience our coffeehouse-style coffee and tea. One well-behaved family pet per room is welcome at Red Roof Inn & Suites Chestertown.
DO NOT WASTE YOUR MONEY
Reviewed By bestyw2022It was so awful staying there. The room smelled like marijuana. The vending machine's are empty. They wont open the pool there excuse is covid & when I went to look at the pool it was so nasty look like it haven't been cleaned in years! The rooms are outta date needs a upgrade really bad. While I was staying the hot water had stopped working for the whole day and they wasn't trying to give me a refund. Overall a horrible experience there. Dont spend your money there next door is way nicer and just done a makeover. I wish i could give this place 0 stars!
5. The Inn at Mitchell House
Overall Ratings
5 based on 100 reviews
Conveniently located on Maryland's Eastern Shore between Chestertown and Rock Hall in Kent County, this lovely 18th-century manor home sits like a jewel on 12 manicured acres. The Chesapeake Bay is a mere 1/2 mile away, where guests may use the private beach and full services of the Tolchester Marina. The Inn's six guest rooms, two parlors, screened porch, and numerous fireplaces provide a casual and friendly atmosphere. Our new "Stones Throw" cottage is the perfect romantic getaway or retreat.
Relaxing getaway in great location
Reviewed By H4989KYjimgAfter more than 30 years since our first visit, we returned to the Inn at Mitchell to find it was better than ever! Innkeepers Jim and Tracy Stone are long-time friends and continue to amaze with simple beauty and charm, historic and rustic décor, and really good breakfasts!!!!! Our room was beautifully appointed, spacious and comfortable, and we really enjoyed the bathroom with shower. We also enjoyed the short drive through the countryside to/from the quaint and easy-to-walk-around streets and waterfront of historic Chestertown -- including catching up on some of the interesting history of the area (don't miss out on Caulk's Field!). We hated to leave - but had quick access to see friends in Annapolis for lunch, visit the Naval Academy in the afternoon, and still have an easy ride to BWI to catch our flight home. Can't wait to visit again -- much sooner this time!
6. Driftwood Inn
Overall Ratings
4 based on 2 reviews
We offer guests outstanding service and a comfortable stay all at the most affordable prices in town. We are the most budget friendly motel in town to give you the most bang for your buck while visiting Chestertown. This 28-room Inn conveniently located in peaceful Chestertown, a historic colonial town by the sparkling waters of the Chester River. This motel is located just within walking distance from Washington College. It offers free Wi-Fi and a 24-hour front desk. Downtown Chestertown, Maryland is 1 mile from the motel. The Driftwood Inn has colonial rooms decorated in rustic wood and soft neutral colors. All rooms include a cable TV with HBO channels, a microwave, refrigerator, and free parking right in front of your room.
Dated but clean
Reviewed By SpyderWitchThis is an inexpensive motel. No frills. If you are looking for an inexpensive place to sleep and move on; this will fit the bill. It is clean. The bathrooms have been updated but not the main sleeping area.
