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Find hotels in Chestertown, MD from $53
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Compare 597 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.
150 Scheeler Road, Chestertown, MD, 21620
Fully refundableReserve now, pay when you stay
The price is $141 per night from Jun 4 to Jun 5
$141
per night
Jun 4 - Jun 5
0.64 mi from city center
8.4/10 Very Good! (597 reviews)
"Beautiful rooms, beautiful property! Continental breakfast was the best we have ever had. So much variety & great products"
Reviewed on May 21, 2023
160 Scheeler Rd, Chestertown, MD, 21620
Fully refundableReserve now, pay when you stay
The price is $119 per night from Jun 4 to Jun 5
$119
per night
Jun 4 - Jun 5
0.58 mi from city center
7.2/10 Good! (199 reviews)
"The check in staff was terrific & was able to change rooms quickly as I had mistakenly booked a rm. w/one bed instead of 2. Explained why there was no breakfast area & their inability to change the website. We were fine as there was coffee maker in room :-)"
Reviewed on May 15, 2023
609 Washington Avenue, Chestertown, MD, 21620
The price is $72 per night from May 31 to Jun 1
$72
per night
May 31 - Jun 1
0.25 mi from city center
4.8/10 (150 reviews)
"Very cleaned and reasonable"
Reviewed on Jun 27, 2022
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4928 Eastern Neck Rd, Rock Hall, MD, 21661
The price is $236 per night from Jun 12 to Jun 13
$236
per night
Jun 12 - Jun 13
11.32 mi from city center
10/10 Exceptional! (41 reviews)
"Many activity options."
Reviewed on May 15, 2023
5681 South Hawthorne Avenue, Rock Hall, MD, 21661
The price is $167 per night from Jun 5 to Jun 6
$167
per night
Jun 5 - Jun 6
11.02 mi from city center
9.2/10 Wonderful! (81 reviews)
"Very glad we found this place."
Reviewed on May 13, 2023
Chestertown, MD
The price is $125 per night from Jun 1 to Jun 2
$125
per night
Jun 1 - Jun 2
0.5 mi from city center
10/10 Exceptional! (51 reviews)
"Fantastic location, gorgeous space, and great host!"
Reviewed on May 26, 2023
Chestertown, MD
The price is $110 per night from May 31 to Jun 1
$110
per night
May 31 - Jun 1
2.18 mi from city center
9.8/10 Exceptional! (40 reviews)
Beautiful, Clean and Tranquil
"This was our second stay at this Vrbo in Chestertown. It was just as perfect for our second stay. It is very clean, quiet and comfortable and in a beautiful location."
Reviewed on May 18, 2023
Centreville, MD
12.53 mi from city center
10/10 Exceptional! (2 reviews)
Paradise
"Everything was wonderful & we didn't want to leave! What a Gem! Thank you!"
Reviewed on Jul 5, 2022
Rock Hall, MD
11.41 mi from city center
10/10 Exceptional! (25 reviews)
Rock Hall
"A very nice property"
Reviewed on Oct 25, 2022
Middle River, MD
19.06 mi from city center
10/10 Exceptional! (12 reviews)
Beautiful location
"This house met our goal- peace and relaxation on the water. Huge beautiful birds and water activities you can engage in."
Reviewed on Apr 21, 2023
Rock Hall, MD
10.75 mi from city center
10/10 Exceptional! (22 reviews)
Downrigging weekend October 2022
"Stayed in Rock Hall so we could go to Chesterton for the Sultana Downrigging weekend. Fun weekend seeing the tall ships. House was immaculate. Very comfortable. Highly recommend this house if you are looking in the area for a rental."
Reviewed on Nov 14, 2022
Rock Hall, MD
The price is $201 per night from May 31 to Jun 1
$201
per night
May 31 - Jun 1
11.01 mi from city center
Rock Hall, MD
10.71 mi from city center
10/10 Exceptional! (8 reviews)
Great support from manager
"We had a small hiccup during check in The manager responded quickly and resolved the problem to our satisfaction"
Reviewed on May 8, 2023
Rock Hall, MD
10.56 mi from city center
10568 Cliff Rd, Chestertown, MD, 21620
7.88 mi from city center
9.4/10 Exceptional! (44 reviews)
"Plenty of privacy"
Reviewed on Feb 15, 2022
Rock Hall, MD
11.49 mi from city center
10/10 Exceptional! (62 reviews)
Perfect getaway
"My husband and I love visiting Rock Hall and this was our first time staying at this home. It is very nicely decorated and has all of the necessary amenities. We were so pleased with this stay, this will definitely be on our favorites list"
Reviewed on Apr 18, 2023
Middle River, MD
18.4 mi from city center
9.8/10 Exceptional! (34 reviews)
Great place for a family vacation
"Good setup for a family get together. 2 grandparents in big bedroom on the main floor. 2 parents and 2 kids in 3 upstairs bedrooms. Table big enough to seat entire family and a few guests. Great open kitchen. Big family room and rear deck have great water views. We enjoyed the kayaks, inflatable ..."
Reviewed on May 15, 2023
Rock Hall, MD
10.95 mi from city center
10/10 Exceptional! (3 reviews)
Sailing through History.....
"We were five retired teachers traveling to the Eastern Shore of Maryland with scheduled stops for Annapolis, St. Michaels, and Easton. Rock Hall was a perfect spot to make day trips to enjoy these locations. The house itself is perfect, five bedrooms so we each had our own room, two full baths, and ..."
Reviewed on May 6, 2023
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
Super 8 by Wyndham Havre De Grace Aberdeen Area
929 Pulaski Hwy, I-95 Exit 89, Havre De Grace, MD, 21078The price is $53 per night from Jun 11 to Jun 12$53per nightJun 11 - Jun 126.6/10 (689 reviews)
4 Star Hotels
1 properties
3 Star Hotels
22 properties
Stay near popular Chestertown attractions
- Washington College
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 hotels information
Number of reviews | 1,371 |
|---|---|
Accommodation | 597 hotels |
Lowest Price | $53 |
Highest Price | $236 |
Frequently asked questions
Recent reviews of Chestertown hotelsExpedia verified reviews
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center5/5 Excellent"All very good"A verified traveler stayed at Best Western Plus Hotel & Conference CenterPosted 12 hours ago
Stay near popular Chestertown attractions
- Washington College
- River Arts Chestertown
- Wilmer Park
- Rolphs Wharf Marina
- Garfield Center for the Arts at the Prince Theater
- Historical Society of Kent County Maryland
- U.S. Naval Academy
- Chesapeake Bay Bridge
- Ripken Stadium
- Sandy Point State Park
- White Marsh Mall
- Fort McHenry
- Cedar Lane Regional Park
- Havre de Grace Promenade
- Harford Community College
- Rock Hall Harbor
- Elk Neck State Park
- Liriodendron Mansion
- Queenstown Premium Outlets
- Annapolis Maritime Museum
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
Chestertown Hotels by Brand
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More Popular Hotels in Maryland
- Hilton Garden Inn Baltimore/White Marsh
- Red Roof Inn Aberdeen
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- Wingate by Wyndham Bel Air I-95 Exit 77A
- Hampton Inn & Suites Edgewood/Aberdeen-South, MD
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Quality Inn
- Hilton Garden Inn Kent Island
- SpringHill Suites Baltimore White Marsh/Middle River
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- Super 8 by Wyndham Havre De Grace Aberdeen Area
- Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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