Photo by Assya A
Find hotels in Chestertown, MD from $62
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check Chestertown hotel prices
Tonight |
Tomorrow night |
This weekend |
Next weekend |
Compare 997 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, (673)
The price is $119
$132 total
includes taxes & fees
May 28 - May 29
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.4 out of 10, Good, (267)
The price is $76
$85 total
includes taxes & fees
May 29 - May 30
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
7.6 out of 10, Good, (4)
The price is $132
$151 total
includes taxes & fees
May 23 - May 24
Save an average of 15% on thousands of hotels when you're signed in
Driftwood Inn
Driftwood Inn
5.0 out of 10, (159)
The price is $64
$70 total
includes taxes & fees
May 23 - May 24
Inn at Huntingfield Creek
Inn at Huntingfield Creek
10.0 out of 10, Exceptional, (44)
The price is $230
$255 total
includes taxes & fees
May 23 - May 24
Mariners Motel
Mariners Motel
9.4 out of 10, Exceptional, (85)
The price is $167
$185 total
includes taxes & fees
May 23 - May 24
BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
The price is $175
$271 total
includes taxes & fees
May 24 - May 25
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
The price is $110
$164 total
includes taxes & fees
May 27 - May 28
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 $201
$394 total
includes taxes & fees
May 23 - May 24
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.
More cheap stays in Chestertown
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road, Edgewood, MD
The price is $62 per night from May 23 to May 24
$62
$70 total
includes taxes & fees
May 23 - May 24
7.4/10 Good! (971 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 | 5,497 |
---|---|
Accommodation | 997 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
"I’ve stayed here before so it was familiar and consistent with my expectations. However, for a non-Baltimorean it is not the easiest place to find, GPS or not."
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Posted 12 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 Wilmer Park
- Hotels near Historical Society of Kent County Maryland
- Hotels near Crumpton Auction
- Hotels near Baltimore Cruise Terminal
- Hotels near U.S. Naval Academy
- Hotels near Sandy Point State Park
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Ripken Stadium
- Hotels near White Marsh Mall
- Hotels near Fort McHenry
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Cedar Lane Regional Park
- Hotels near Susquehanna River
- Hotels near Havre de Grace Promenade
- 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 (421)
- Apartments in Chestertown (71)
- 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 (1)
- Lodges in Chestertown (1)
Chestertown Hotels by Brand
Other Hotels near Chestertown, Maryland
- Hotels in Annapolis
- Hotels in Dover
- Hotels in St. Michaels
- Hotels in Delaware Beaches
- Hotels in Aberdeen
- Hotels in Easton
- Hotels in Elkton
- Hotels in Glen Burnie
- Hotels in White Marsh
- Hotels in Edgewood
- Hotels in Chesapeake Bay
- Hotels in Bel Air
- Hotels in Grasonville
- Hotels in Havre De Grace
- Hotels in Kent Island
- Hotels in Stevensville
- Hotels in Eastern Shore
- Hotels in Middletown
- Hotels in North East
- Hotels in Rock Hall
More Popular Hotels in Maryland
- Fairfield Inn & Suites by Marriott White Marsh
- WoodSpring Suites Baltimore White Marsh - Nottingham
- Hyatt Place Kent Narrows & Marina
- Annapolis Waterfront Hotel, Autograph Collection
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Country Inn & Suites by Radisson, Baltimore North, MD
- Hilton Garden Inn Baltimore/White Marsh
- Hampton Inn Baltimore/White Marsh
- Hampton Inn Baltimore/Glen Burnie
- The Inn at Henderson's Wharf, Ascend Hotel Collection
- La Quinta Inn & Suites by Wyndham Aberdeen-APG
- Courtyard by Marriott Baltimore Downtown/McHenry Row
Expedia's Latest Trends
Hotels
Hotels in WaldorfPet-friendly Hotels in Ocean CityHotels in HagerstownHotels in Silver SpringCheap Hotels in Silver SpringHotels in Ocean CityOceanfront Hotels in Ocean CityCheap Hotels in Ocean CityBeach Hotels in Ocean CityHotels in RockvilleHotels in SalisburyHotels in AberdeenHotels in AnnapolisHotels in St. MichaelsHotels in CumberlandHotels in College ParkHotels in FrederickOceanfront Hotels in AnnapolisHotels in Bel Air
Cars
Packages
Vacation Rentals