Best places: Hotels in Chestertown, United States

A high-end property offering refined rooms & suites, plus a posh day spa, 2 pools & stylish dining.

Victorian bed-&-breakfast offering homey, antiques-furnished lodging with free Wi-Fi & cable TV.

Polished suites, some featuring city views, in a refined boutique hotel offering breakfast.

Waterfront, Georgian-style B&B with refined rooms, plus a library, a music room & a sun room.

Elegant rooms & suites in a posh property offering a spa, plus a bistro with a wine cellar.

Elegant rooms with period-style decor in 3 historic inns, plus an English-style pub & a gym.

Elegant 18th-century home offering charming quarters, plus home-cooked breakfast & refreshments.

Unfussy rooms & suites with iPod docks in a laid-back hotel offering a heated indoor pool & a gym.

Informal hotel offering complimentary breakfast & parking, plus a gym, a hot tub & an indoor pool.

B&B offering luxe rooms with whirlpool tubs & free Wi-Fi in historic row homes off a courtyard.

Modern high-end hotel with a laid-back American restaurant, a 24/7 fitness center & a sauna.

Posh lodging in a 1914 pier building, offering chic rooms, an elegant Italian restaurant & a bar.

🫤 This venue was soooo difficult for our group to work with. They consistently lost or distorted the information they were given. They were pricey compared to other venues we've used. Their food was good, and the staff was efficient, but the lead staff member was quite rude at the end of the night pu...

Quaint country-chic lodging featuring a restaurant & a cafe, plus a spa, a gym & bay views.

Casual lodging offering free Wi-Fi, breakfast & parking, plus an indoor pool & a fitness center.

Bayfront property featuring an elegant 19th-century B&B, a swim dock & free use of kayaks.

Sophisticated hotel featuring nautical-themed rooms, plus a bar/grill, a spa & an outdoor pool.

Relaxed rooms in a straightforward hotel offering free breakfast & an indoor pool, plus a gym.

High-end, waterfront hotel offering butler service & complimentary continental breakfast.

Refined quarters in an upmarket bayside inn offering an outdoor pool, a marina & a restaurant.