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location Chestertown is highly rated for Sports and Universities by 542 people
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Check prices on hotels in Chestertown
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Nov 18 - Nov 19
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Nov 23 - Nov 25
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Nov 30 - Dec 2
Top 10 Hotels in Chestertown
John L Stam House3.0 out of 5.0
John L Stam House
114 Washington Ave, Chestertown John L Stam HouseSituated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 25.9 mi (41.7 km) from Queenstown Premium Outlets.
$190 per night for 2 guests
Holiday Inn Express Hotel & Suites Chestertown2.5 out of 5.0
Holiday Inn Express Hotel & Suites Chestertown
150 Scheeler Road, Chestertown Holiday Inn Express Hotel & Suites ChestertownSituated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 27 mi (43.5 km) from Queenstown Premium Outlets.
$83 per night for 2 guests
Driftwood Inn2.0 out of 5.0
Driftwood Inn
609 Washington Avenue, Chestertown Driftwood InnSituated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.
$59 per night for 2 guests
Great Oak Manor3.5 out of 5.0
Great Oak Manor
10568 Cliff Rd, Chestertown Great Oak ManorNestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.
$169 per night for 2 guests
Stunning Home on a 25-acre Private Woodland Estate
Stunning Home on a 25-acre Private Woodland Estate
, Chestertown Stunning Home on a 25-acre Private Woodland EstateSituated in Chestertown, this historic vacation home is in the same area as Washington College.
Stunning Home on a 25-acre Private Woodland EstateGet Rates
Annapolis home with many amenities3.0 out of 5.0
Annapolis home with many amenities
1013 Magothy Park Ln, Annapolis Annapolis home with many amenitiesSituated in the suburbs, this villa is close to Sandy Point State Park and Chesapeake Bay Bridge. Area attractions also include U.S. Naval Academy and William ...
$198 per night for 2 guests
Extended Stay America Baltimore - Bel Air- Aberdeen2.5 out of 5.0
Extended Stay America Baltimore - Bel Air- Aberdeen
1361 James Way, Bel Air Extended Stay America Baltimore - Bel Air- AberdeenSituated in Bel Air, this hotel is within 9 mi (15 km) of Ripken Stadium, Cal Ripken Museum, and Harford Community College. Aberdeen Proving Ground and Liriodendron ...
$58 per night for 2 guests
La Quinta Inn & Suites Edgewood / Aberdeen-South2.5 out of 5.0
La Quinta Inn & Suites Edgewood / Aberdeen-South
2112b Emmorton Park Rd, Edgewood La Quinta Inn & Suites Edgewood / Aberdeen-SouthSituated in Edgewood, this hotel is within 12 mi (20 km) of Harford Mall, Ripken Stadium, and Harford Community College. Aberdeen Proving Ground is 11.8 mi (19 ...
$79 per night for 2 guests
Inn at Haven Harbour3.0 out of 5.0
Inn at Haven Harbour
20880 Rock Hall Ave., Rock Hall Inn at Haven HarbourSituated on the waterfront, this bed & breakfast is 13.7 mi (22 km) from Washington College.
$101 per night for 2 guests
Mariners Motel2.0 out of 5.0
Mariners Motel
5681 South Hawthorne Avenue, Rock Hall Mariners MotelSituated near the bay, this motel is within a 15-minute walk of Rock Hall Harbor, The Mainstay, and Ferry Park. Garfield Center for the Arts at the Prince Theater ...
$97 per night for 2 guests
Hotels with reviews mentioning Chestertown
See all hotels near Chestertown
Holiday Inn Express Hotel & Suites Chestertown
Hotel was very clean, comfortable and convenient to Chestertown and Washington College.
John L Stam House
This B&B is walking distance to Washington College, the Chester River and the quaint stores and coffee shops in Chestertown.
Holiday Inn Express Hotel & Suites Chestertown
And Chestertown is a hidden gem!
Great Oak Manor
- Breakfast buffet was tasty and better than a continental breakfast from the local Holiday Inn Express.- Quick drive to Chestertown for shopping and food.- Quick drive to Rock Hall for crabs.
Search Hotels near Top Chestertown Attractions
Recent Reviews in Chestertown
Expedia Verified Review
Convenient & well located. Free breakfast was good. Only downside is the exterior entrance to the rooms
A verified traveler stayed at Best Western Kent Narrows Inn
Posted 1 day ago
Expedia Verified Review
The bed in room 202 was horrible ! Needs a new mattress ! Rolled right to the middle of the king bed !
A verified traveler from White Marsh MD stayed at Fairfield Inn & Suites by Marriott Baltimore
Posted 2 days ago
Where to stay in Chestertown
Hotel Class
Near an Attraction
- Washington College
- Wilmer Park
- Rolphs Wharf Marina
- River Arts Chestertown
- Garfield Center for the Arts at the Prince Theater
- Historical Society of Kent County Maryland
- Fort McHenry
- U.S. Naval Academy
- Aberdeen Proving Ground
- Chesapeake Bay Bridge
- White Marsh Mall
- Korean War Memorial
- Essex Marina
- Annapolis Maritime Museum
- Sandy Point State Park
- Queenstown Premium Outlets
- Annapolis Sailing School
- Elk Neck State Park
- Harford Mall
- Ripken Stadium
Hotel Theme
- Hotels with Air Conditioning (9)
- Non-Smoking Hotels (7)
- Hotels with Free Parking (6)
- Hotels with Free Wifi (6)
- Hotels with Restaurants (5)
- Adventure Hotels (5)
- Hotels with Free Breakfast (5)
- Romantic Hotels (5)
- Family Hotels (5)
- Hotels with Fireplaces (4)
- Pet-friendly Hotels (4)
- Beach Hotels (4)
- Hotels with a Pool (3)
- Hotel with a Concierge (3)
- Hotels with an Outdoor Pool (3)
- Historic Hotels (3)
- Hotels with a Gym (3)
- Hotels with Laundry Facilities (3)
- Hotel Wedding Venues (2)
- Cheap Hotels (2)
- Hotels with an Indoor Pool (2)
- Hotels with Bars (1)
- Shopping Hotels (1)
- Golf Hotels (1)
- Business Hotels (1)
- Hotels with Suites (1)
- Resorts & Hotels with Spas (1)
- Oceanfront Hotels (1)
- Hotels with Kitchenettes (1)
- Arcade Hotels (1)
- Luxury Hotels (1)
Visiting Chestertown
Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art.
- There are 9 hotels and other accommodations in Chestertown
- The closest major airport is in Baltimore, MD (MTN-Martin State), 19.5 mi (31.4 km) from the city center
- The next closest is in Easton, MD (ESN-Easton - Newnam), 27.3 mi (43.9 km) away
Sightseeing and Staying in Chestertown
The city's cultural venues include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. The university setting is a highlight of the city and Washington College is worth a campus tour. A couple of additional sights to add to your agenda are Wilmer Park and Rolphs Wharf Marina.
As you plan your vacation, you'll find 9 hotels and other lodging options available to select from in Chestertown. Below are highly ranked ones based on our user reviews:
- John L Stam House - With a stay at this 3-star bed & breakfast, guests can enjoy access to free breakfast and free parking, along with free WiFi. It's a favorite with Expedia travelers for its breakfast and proximity to shopping.
- Holiday Inn Express Hotel & Suites Chestertown - Our customers like the breakfast and quiet location at this hotel. With a stay at this 2.5-star hotel, guests can enjoy access to free breakfast and an indoor pool, along with free WiFi.
- Quality Suites - This 2.5-star hotel features free breakfast, an indoor pool, and free WiFi.
Dressing for Chestertown
- Between January and March, you can expect the daytime average to be around 58°F and the nighttime average to be 25°F
- From April to June, temperatures average about 85°F during the day and 39°F at night
- July through September averages 87°F during the day and 53°F at night
- In October-December, the average temperature is 73°F during the day and 28°F at night
- Chestertown gets about 1.42 inches of rain per year
- Hottest months are usually July and August with an average temperature of 85°F, while the coldest months are January and February with an average of 28°F
More Hotels in Chestertown
- Chester River Waterfront
- Country Inn & Suites by Radisson
- Quality Suites
- La Quinta Inn & Suites Baltimore N / White Marsh
- Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water
- Red Roof Inn Edgewood
- The Inn at Chesapeake Bay Beach Club
- Red Roof Inn Aberdeen
- Inn at Mitchell House
- Best Western Plus Hotel & Conference Center
- Americas Best Value Inn Baltimore
- La Quinta Inn & Suites Aberdeen-APG
Hotels Near Chestertown, Maryland
- St. Michaels Hotels
- Easton Hotels
- Aberdeen Hotels
- Elkton Hotels
- Glen Burnie Hotels
- Bel Air Hotels
- White Marsh Hotels
- Edgewood Hotels
- Grasonville Hotels
- North East Hotels
- Middletown Hotels
- Havre De Grace Hotels
- Rosedale Hotels
- Harrington Hotels
- Stevensville Hotels
- Chesapeake Bay Hotels
- Smyrna Hotels
- Eastern Shore Hotels
- Rock Hall Hotels
- Chesapeake City Hotels
More accommodations in Chestertown
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