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Find hotels in Chestertown, MD from CA $85
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Top 10 Chestertown hotels and places to stay
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (671)
The price is CA $168
CA $186 total
includes taxes & fees
May 20 - May 21
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (264)
The price is CA $104
CA $116 total
includes taxes & fees
May 21 - May 22
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
7.6 out of 10, Good, (4)
The price is CA $181
CA $206 total
includes taxes & fees
May 16 - May 17
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Driftwood Inn
Driftwood Inn
5.0 out of 10, (159)
The price is CA $87
CA $96 total
includes taxes & fees
May 16 - May 17
Inn at Huntingfield Creek
Inn at Huntingfield Creek
10.0 out of 10, Exceptional, (44)
The price is CA $313
CA $348 total
includes taxes & fees
May 19 - May 20
Mariners Motel
Mariners Motel
9.4 out of 10, Exceptional, (85)
The price is CA $228
CA $253 total
includes taxes & fees
May 19 - May 20
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
The price is CA $239
CA $365 total
includes taxes & fees
May 16 - May 17
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (58)
The price is CA $134
CA $207 total
includes taxes & fees
May 16 - May 17
Carriage House Hideaway in Middle of Chestertown
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, (76)
200 steps to the beach!
200 steps to the beach!
10.0 out of 10, Exceptional, (73)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (37)
Cute waterfront apartment -- 8 min from the beach!
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, (5)
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (77)
Waterfront Oasis w/ Private Dock, 3BR/2BA
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (19)
Rambling Victorian Beach House on Maryland's Eastern Shore
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
This is truly a Baydream!
This is truly a Baydream!
10.0 out of 10, Exceptional, (27)
Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, (1)
The price is CA $275
CA $537 total
includes taxes & fees
May 20 - May 21
Serene Waterfront Cottage with dock and gorgeous views.
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.4 out of 10, Exceptional, (26)
Charming Chestertown Waterfront Cottage
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, (58)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More cheap stays in Chestertown
More cheap stays in Chestertown
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct, Rosedale, MD
The price is CA $129 per night from May 19 to May 20
CA $129
CA $149 total
includes taxes & fees
May 19 - May 20
7.2/10 Good! (1,003 reviews)
Hotels in Chestertown with star rating
Hotels in Chestertown with star rating
Hotels near Popular Chestertown Attractions
Hotels near Popular Chestertown Attractions
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Recent Reviews in Chestertown
Recent Reviews in Chestertown
5/5 Excellent
"Clean environment, great breakfast, kind customer service. Beds were very firm."
A verified traveller stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 1 day ago
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Hotels near Popular Chestertown Attractions
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Hotels near Chestertown Airports
Other Hotels near Chestertown, Maryland
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Explore more hotels
- Holiday Inn Express White Marsh, An IHG Hotel
- Fairfield Inn & Suites by Marriott White Marsh
- Hilton Garden Inn Baltimore/White Marsh
- Hampton Inn Baltimore/White Marsh
- La Quinta Inn & Suites by Wyndham Aberdeen-APG
- The Inn at Henderson's Wharf, Ascend Hotel Collection
- Hampton Inn Baltimore/Glen Burnie
- Courtyard by Marriott Baltimore Downtown/McHenry Row