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Find hotels in Chestertown, MD from SAR70
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Compare 993 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (676)
The price is SAR 459
SAR 505 total
includes taxes & fees
28 Jum. I - 29 Jum. I
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (268)
The price is SAR 319
SAR 350 total
includes taxes & fees
28 Jum. I - 29 Jum. I
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
7.6 out of 10, Good, (4)
The price is SAR 525
SAR 593 total
includes taxes & fees
28 Jum. I - 29 Jum. I
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Driftwood Inn
Driftwood Inn
5.0 out of 10, (159)
The price is SAR 238
SAR 264 total
includes taxes & fees
28 Jum. I - 29 Jum. I
Inn at Huntingfield Creek
Inn at Huntingfield Creek
10.0 out of 10, Exceptional, (44)
The price is SAR 861
SAR 956 total
includes taxes & fees
28 Jum. I - 29 Jum. I
Mariners Motel
Mariners Motel
9.4 out of 10, Exceptional, (85)
The price is SAR 582
SAR 646 total
includes taxes & fees
29 Jum. I - 30 Jum. I
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
The price is SAR 656
SAR 1,002 total
includes taxes & fees
28 Jum. I - 29 Jum. I
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
The price is SAR 413
SAR 616 total
includes taxes & fees
28 Jum. I - 29 Jum. I
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, (74)
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 SAR 755
SAR 1,476 total
includes taxes & fees
28 Jum. I - 29 Jum. I
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, (59)
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.
Stay near popular Chestertown attractions
Washington College
4/5(13 reviews)
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.
Frequently asked questions
Recent reviews of Chestertown hotelsExpedia verified reviews
5/5 Excellent
Good hotel
"Great room. Good location. Breakfast was good "
A verified traveler stayed at Country Inn & Suites by Radisson, Baltimore North, MD
Posted 2 days ago
Stay near popular Chestertown attractions
- Washington College
- Rolphs Wharf Marina
- River Arts Chestertown
- Garfield Center for the Arts at the Prince Theater
- Historical Society of Kent County Maryland
- Wilmer Park
- Crumpton Auction
- Baltimore Cruise Terminal
- U.S. Naval Academy
- Sandy Point State Park
- Chesapeake Bay Bridge
- Ripken Stadium
- Annapolis City Dock
- White Marsh Mall
- Fort McHenry
- Cedar Lane Regional Park
- Susquehanna River
- Navy-Marine Corps Memorial Stadium
- Havre de Grace Promenade
- Maryland State House
More Hotel Options in Chestertown
- Adventure Hotels (5)
- Beach Hotels (4)
- Business Hotels (1)
- Cheap Hotels (2)
- Family Hotels (5)
- Golf Hotels (1)
- Historic Hotels (3)
- Hotel Wedding Venues (2)
- Hotel with a Concierge (3)
- Hotels with Bars (1)
- Hotels with Free Parking (6)
- Hotels with WiFi (6)
- Hotels with a Pool (3)
- Hotels with an Indoor Pool (2)
- Hotels with smoking rooms (1)
- Luxury Hotels (1)
- Pet-friendly Hotels (4)
- Resorts & Hotels with Spas (1)
- Romantic Hotels (5)
- Shopping Hotels (1)
Chestertown Hotels by Brand
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Explore more hotels
- Holiday Inn Express White Marsh, An IHG Hotel
- Fairfield Inn & Suites by Marriott White Marsh
- WoodSpring Suites Baltimore White Marsh - Nottingham
- Hyatt Place Kent Narrows & Marina
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Hilton Garden Inn Baltimore/White Marsh
- Annapolis Waterfront Hotel, Autograph Collection
- Country Inn & Suites by Radisson, Baltimore North, MD
- Hampton Inn Baltimore/White Marsh
- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
- Red Roof Inn Baltimore South - Glen Burnie
- La Quinta Inn & Suites by Wyndham Aberdeen-APG