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Find hotels in Chestertown, MD from $62
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Compare 988 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, 680 reviews
The price is $128
$142 total
includes taxes & fees
Jun 27 - Jun 28
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, 279 reviews
The price is $81
$90 total
includes taxes & fees
Jun 23 - Jun 24
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
7.6 out of 10, Good, 4 reviews
The price is $136
$152 total
includes taxes & fees
Jun 17 - Jun 18
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Driftwood Inn
Driftwood Inn
5.0 out of 10, 160 reviews
The price is $64
$70 total
includes taxes & fees
Jun 17 - Jun 18
Inn at Huntingfield Creek
Inn at Huntingfield Creek
10.0 out of 10, Exceptional, 44 reviews
The price is $230
$255 total
includes taxes & fees
Jun 18 - Jun 19
Mariners Motel
Mariners Motel
9.4 out of 10, Exceptional, 85 reviews
The price is $167
$185 total
includes taxes & fees
Jun 17 - Jun 18
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 18 reviews
The price is $175
$272 total
includes taxes & fees
Jun 17 - Jun 18
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
The price is $110
$164 total
includes taxes & fees
Jun 17 - Jun 18
Carriage House Hideaway in Middle of Chestertown
Carriage House Hideaway in Middle of Chestertown
10.0 out of 10, Exceptional, 76 reviews
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, 38 reviews
Cute waterfront apartment -- 8 min from the beach!
Cute waterfront apartment -- 8 min from the beach!
10.0 out of 10, Exceptional, 5 reviews
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 reviews
Waterfront Oasis w/ Private Dock, 3BR/2BA
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, 20 reviews
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 reviews
Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall Harbor
10.0 out of 10, Exceptional, 1 review
The price is $219
$416 total
includes taxes & fees
Jun 27 - Jun 28
Serene Waterfront Cottage with dock and gorgeous views.
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, 35 reviews
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, 28 reviews
Charming Chestertown Waterfront Cottage
Charming Chestertown Waterfront Cottage
10.0 out of 10, Exceptional, 59 reviews
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
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct, Rosedale, MD
The price is $85 per night from Jul 4 to Jul 5
$85
$98 total
includes taxes & fees
Jul 4 - Jul 5
7.2/10 Good! (1,004 reviews)
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.
Chestertown Travel Info
Number of reviews | 5,607 |
---|---|
Accommodation | 988 hotels |
Highest price | $230 |
Lowest price | $62 |
Reasons to visit | Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College |
Frequently asked questions
Recent reviews of Chestertown hotelsExpedia verified reviews
5/5 Excellent
"Everything was clean and tidy. I liked the flooring in the room (no carpet). The bed was comfortable and the pillows were perfect. Breakfast selection and quality were very good. The whole hotel was nicely decorated."
A verified traveler stayed at Hyatt Place Kent Narrows & Marina
Posted 8 hours ago
Stay near popular Chestertown attractions
- Hotels near Washington College
- Hotels near Rolphs Wharf Marina
- Hotels near River Arts Chestertown
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Historical Society of Kent County Maryland
- Hotels near Wilmer Park
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay Bridge
- Hotels near Sandy Point State Park
- Hotels near Ripken Stadium
- Hotels near Annapolis City Dock
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Cedar Lane Regional Park
- Hotels near Susquehanna River
- Hotels near Fort McHenry
- Hotels near White Marsh Mall
- Hotels near Rock Hall Harbor
- Hotels near Harford Community College
More Hotel Options in Chestertown
- 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 & Resorts for Couples (5)
- Hotels with Air Conditioning (9)
- Hotels with Bars (1)
- Hotels with Fireplaces (4)
- Hotels with Free Breakfast (5)
- Hotels with Free Parking (6)
- Hotels with Free Wifi (6)
- Hotels with Kitchenettes (1)
- Hotels with Laundry Facilities (3)
- Hotels with Restaurants (5)
- Hotels with Suites (1)
- Hotels with a Gym (3)
- Hotels with a Pool (3)
- Hotels with a View (2)
- Hotels with an Indoor Pool (2)
- Hotels with an Outdoor Pool (3)
- Hotels with smoking rooms (1)
- Luxury Hotels (1)
- Non-Smoking Hotels (7)
- Oceanfront Hotels (1)
- Pet-friendly Hotels (4)
- Resorts & Hotels with Spas (1)
- Romantic Hotels (5)
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown (411)
- Apartments in Chestertown (74)
- Cottages in Chestertown (39)
- Guest Houses in Chestertown (15)
- Motels in Chestertown (11)
- RV Parks in Chestertown (9)
- B&B in Chestertown (7)
- Houseboats in Chestertown (7)
- Villas in Chestertown (6)
- Condo Rentals in Chestertown (5)
- Farmstay in Chestertown (3)
- Cabin Rentals in Chestertown (2)
- Lodges in Chestertown (1)
Chestertown Hotels by Brand
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More Popular Hotels in Maryland
- Hampton Inn Baltimore Bayview Campus
- Holiday Inn Express White Marsh, An IHG Hotel
- WoodSpring Suites Baltimore White Marsh - Nottingham
- Annapolis Waterfront Hotel, Autograph Collection
- Hyatt Place Kent Narrows & Marina
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- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
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