Top Hotels in Chestertown
Find the Top Hotels in Chestertown – 3+ Quality Options from Leading Providers
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8.2
Great6161 reviews10
MapView on map1.3 mi from City Center400 yd from Kent Plaza Shopping Center
From
US$ 92
/night
- Fitness center with modern equipment
- 24-hour bilingual front desk service
- Pet-friendly accommodations available
Bed & Breakfast
8.8
Great3333 reviews10
MapView on map1.5 mi from City Center
From
US$ 337
/night
- Adults-only cottages with fireplaces and spa tubs
- Daily gourmet breakfast with homemade jams and pastries
- Historic gardens with serene walking trails
Hotel
8.0
Great4949 reviews10
- Indoor pool
- Hot tub
- Meeting room
1.3 mi from City Center400 yd from Kent Plaza Shopping Center
From
US$ 75
/night
- Indoor heated pool for year-round fun
- Complimentary breakfast with hot options
- Friendly staff with personalized recommendations
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Top Hotel Picks in Chestertown
How much is a room per night?
The recommended hotels in Chestertown are chosen for their proximity to historical sites and the waterfront. Prices start around $120 per night, with many hotels rated above 8.0/10 on guest reviews, ensuring a good stay near the Historic District and the Chester River.
3 star:
$120-$180
4 star:
$180-$250
5 star:
$250-$400
Top Recommended Boutique Hotels in Chestertown
Chestertown, 2 km from Imagination Alley
This 2-star hotel offers a seasonal outdoor swimming pool and a fitness center, plus free WiFi. New Castle Airport is located 46 miles away.
Aberdeen, 29 miles from Clifton Park
This 3-star hotel includes a fitness center and indoor pool. It is situated near Towson University and is 29 miles from the Korean War Memorial.
Top Recommended Central Hotels in Chestertown
Belcamp, 25 miles from Clifton Park
This 2-star hotel features a fitness center and provides free private parking. It's near Towson University and the Korean War Memorial, both 25 miles away.
Eastern Shore, 632 m from Queen Anne's Museum
Located near Route 50 and Route 301, this hotel offers easy access to sandy beaches and various outdoor activities at Sandy Point State Park.
