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Here is a quick list of Hotels in Chestertown, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Driftwood Inn |
4.7 / 10 (65 Reviews) |
From 57$ | |
| Brampton 1860 |
9.5 / 10 (15 Reviews) |
From 337$ | |
| Quality Suites |
8.3 / 10 (57 Reviews) |
From 75$ | |
| Comfort Inn & Suites Chestertown |
8.1 / 10 (240 Reviews) |
From 92$ |
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Featuring Wi-Fi in public areas, Driftwood Inn Chestertown sits only 1.2 km from Kent Plaza Shopping Center. At the motel, guests will find a golf club to stay active.
This 2-star hotel is about 80 km from New Castle airport and about a 20-minute walk from such cultural venues as the MassoniArt Gallery. Church of the Nazarene is 2.6 km from the property in Chestertown. The Driftwood Inn is also 25 minutes on foot from the Twigs & Teacups shop.
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Brampton 1860
From 337$
Providing 13 rooms, the luxurious Brampton 1860 Bed & Breakfast Chestertown is 2.8 km from Kohl Gallery at Gibson Center for the Arts. Guests of the 5-star hotel can immerse themselves in the tranquillity of the garden, complete with an outdoor seating.
The centre of Chestertown is a 30 minutes' walk of the inn. The Cassinelli Winery & Distillery is also located within 10 minutes' drive of the Brampton 1860 Bed & Breakfast Chestertown. The Pam Foss Sculpture Gallery is also situated around 3 km away.
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Featuring a vending machine and a lift, the 3-star Quality Suites Chestertown hotel is nestled in Chestertown, about a 25-minute walk from the Twigs & Teacups shop. Boasting an indoor swimming pool and a gym, this comfortable hotel offers access to the Cassinelli Winery & Distillery, which is 2.3 km away.
The hotel is a great place to stay due to its prime location in Chestertown. The Pam Foss Sculpture Gallery is within 30 minutes' walk of the Quality Suites in Chestertown.
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Highlighting a banquet hall, suited for gatherings, the perfect Comfort Inn & Suites Chestertown is located nearly 25 minutes' walk from the Cassinelli Winery & Distillery. The 2-star smoke-free hotel in a business neighbourhood features an indoor pool and a fitness centre.
This excellent hotel is 2.4 km from the Twigs & Teacups shop and 2.5 km from Chestertown Historic District. The comfortable Comfort Inn & Suites stands right around the corner from Chesapeake Movies and lies near a river. The accommodation is also in proximity to the Chester River.
Hotels in Chestertown
| Best reviews Hotel ❤️ | Driftwood Inn |
| Family Hotel 👪 | Brampton 1860 |
| Hotel with a view 🔍 | Quality Suites |