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Chestertown Vacation Rentals and Hotels

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We have over 400 properties in the Chestertown, Maryland area.
Please browse our top 30 properties below
Vacation Rentals in the Chestertown/Oxford area. (36 miles away)
Maryland Riverfront Historic Bed & Breakfast Inn #267 From $130/night
1-34 Beds 1-34 Baths Sleeps 1-2 Bed and Breakfast 4 photos
The Robert Morris Inn, dating back to 1710 is one of the oldest historic inns in the United States. Robert Morris, Jr. helped finance the Revolutionary War, numbered George Washington among his friends, and was a signer of the Declaration of Independence, the Articles of Confederation, and the United ...
Vacation Rentals in the Chestertown/Solomons area. (63 miles away)
Bay View Cottage with Firepit and Hot Tub! #2130 From $495/week
2 Beds 1.5 Baths Sleeps 4 Cottage 4 photos Pet Friendly
Watch the sunrise from the bedrooms upstairs. You can see across the bay on the upper deck year round. Relax on the patio where you will catch a glimpse of the bay. The patio has a hot tub and small firepit which are great for the cooler weather. Walk to the beach just a block away. Enjoy the fireplace ...
 
Hotels in the Chestertown area.
 
Comfort Suites Chestertown From $109.99/nt   A 3 Star Hotel! 3 Star Hotel
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The Comfort Suites® hotel is just one mile from Washington College. This Chestertown hotel is minutes from the Eastern Neck National Wildlife Refuge
 
The Fern Lodge Chestertown From $395.03/nt   A 3 Star Hotel! 3 Star Hotel
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In the midst of the majestic Adirondack Mountains, overlooking pristine Friends Lake, there stands a wondrous Guesthouse where luxurious lodgings, sumptuous
 
Comfort Suites Chestertown From $109.99/nt   A 3 Star Hotel! 3 Star Hotel
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The Comfort Suites® hotel is just one mile from Washington College. This Chestertown hotel is minutes from the Eastern Neck National Wildlife Refuge
Hotels in the Chestertown/Edgewood area. (18 miles away)
 
La Quinta Inn & Suites Edgewood / Apg South From $84.00/nt   A 3 Star Hotel! 3 Star Hotel
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The La Quinta Inn and Suites Edgewood is located in Edgewood, Md. Three miles from Exton Golf Course and five and a half miles from Hartford Mall.
 
Hampton Inn and Suites Edgewood/Aberdeen-South MD From $101.16/nt   A 2 Star Hotel! 2 Star Hotel
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The Hampton Inn and Suites@reg; Edgewood/Aberdeen-South is located 25 miles from Baltimore/Washington International Airport.
 
Days Inn Edgewood From $50.40/nt   A 2 Star Hotel! 2 Star Hotel
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Days Inn Edgewood is 18 miles north of Baltimore's Inner Harbor and Oriole's Park at Camden Yards and approximately 40 miles from Baltimore/Washington
 
Best Western Invitation Inn Edgewood From $74.00/nt   A 3 Star Hotel! 3 Star Hotel
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158 handsomely decorated rooms at a full service hotel with easy access to State Route 40 and Interstate 95.
 
Ramada Edgewood From $67.20/nt   A 3 Star Hotel! 3 Star Hotel
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The Ramada Edgewood is located off of Interstate 95, approximately 30 miles from the Baltimore/Washington International Airport. Local attractions include
 
Sleep Inn and Suites Edgewood From $74.99/nt   A 2 Star Hotel! 2 Star Hotel
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Sleep Inn Edgewood is located less than 30 miles from Baltimore, 20 miles from Arundel Mills, and 35 miles from Baltimore/Washington International Airport.
 
Edgewood Hampton Inn From $84.00/nt   A 2 Star Hotel! 2 Star Hotel
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When you come to stay at Hampton Inn® hotel in Baltimore/Edgewood, you're entering a metro area of more than eight million residents.
 
Holiday Inn Express Edgewood-i95 Md From $108.00/nt   A 3 Star Hotel! 3 Star Hotel
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Holiday Inn Express Edgewood is located approximately 30 miles from Baltimore Washington International Airport and Baltimore's Inner Harbor.
Hotels in the Chestertown/Belcamp area. (19 miles away)
 
Belcamp Wingate by Wyndham Aberdeen From $97.76/nt   A 3 Star Hotel! 3 Star Hotel
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The Wingate by Wyndham Aberdeen/Riverside MD offers affordable accommodations conveniently accessible to I-95, approximately 36 miles from Baltimore International
Hotels in the Chestertown/Grasonville area. (19 miles away)
 
Hilton Garden Inn Kent Island Grasonville From $109.66/nt   A 3 Star Hotel! 3 Star Hotel
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Nestled along the edge of the Kent Narrows and Prospect Bay, Maryland, the Hilton Garden Inn Kent Island has private balconies to view the abundant waterfowl
 
Sleep Inn Grasonville From $69.99/nt   A 2 Star Hotel! 2 Star Hotel
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This Sleep Inn is located approximately just two miles from Kent Narrows and 30 miles from Baltimore/Washington International Airport.
 
Best Western Kent Narrows Inn Grasonville From $99.00/nt   A 3 Star Hotel! 3 Star Hotel
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The Best Western Kent Narrows is located conveniently on Routes 50 and 301, on the scenic Eastern Shore of Maryland. The Best Western is centrally located
 
Holiday Inn Express Kent Island Md Grasonville From $76.56/nt   A 2 Star Hotel! 2 Star Hotel
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This hotel is located on the beautiful Eastern Shore of Maryland, along routes 50 and 301, just 15 miles to the east of Annapolis and minutes away from
Hotels in the Chestertown/Joppa area. (20 miles away)
 
Super 8 Motel Joppa From $53.54/nt   A 2 Star Hotel! 2 Star Hotel
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Free high speed internet .
Hotels in the Chestertown/Aberdeen area. (21 miles away)
 
Travelodge Hotel Aberdeen From $46.75/nt   A 2 Star Hotel! 2 Star Hotel
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This Travelodge is located approximately 30 miles from Baltimore Inner Harbor and 40 miles from Baltimore Washington International Airport.
 
Clarion Hotel Aberdeen From $78.99/nt   A 3 Star Hotel! 3 Star Hotel
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Located directly off I-95 the Clarion Hotel in Aberdeen Maryland, home of Cal Ripken Baseball Academy and the Babe Ruth World Series, is the premier full-service
 
Super 8 Aberdeen Md From $54.99/nt   A 2 Star Hotel! 2 Star Hotel
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Super 8 Aberdeen is located approximately two miles from the Aberdeen Ordinance Museum, 34 miles from Baltimore Inner Harbor, and 40 miles northeast of
 
Americas Best Value Inn Aberdeen From $59.00/nt   A 1 Star Hotel! 1 Star Hotel
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Centrally located on the main highway heading north through Aberdeen, the Americas Best Value Inn is situated at a short distance from the Grays Harbor
 
Courtyard By Marriott Aberdeen From $169.00/nt   A 3 Star Hotel! 3 Star Hotel
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Centrally located directly across from Ripken Stadium, our location is convenient to those attending Cal Ripken Baseball Academy, Babe Ruth League World
 
Hilton Garden Inn Aberdeen From $99.00/nt   A 3 Star Hotel! 3 Star Hotel
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The new Hilton Garden Inn Aberdeen is located off the I-95 corridor and close to Aberdeen Proving Ground.
 
Hampton Inn and Suites Aberdeen From $96.91/nt   A 3 Star Hotel! 3 Star Hotel
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The Hampton Inn and Suites Aberdeen is conveniently located near (ABR) Aberdeen Regional Airport.
 
Americas Best Value Inn From $60.00/nt   A 2 Star Hotel! 2 Star Hotel
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The Americas Best Value Inn and Suites Aberdeen Hotel is conveniently located in the Baltimore metropolitan area, close to the University of Maryland.
 
Super 8 Aberdeen North Sd From $59.97/nt   A 2 Star Hotel! 2 Star Hotel
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This Super 8 Motel is situated in the Hub City, across from the Lee Park Municipal Golf Course and Village Bowl Bowling Alley, approximately three miles
 
Super 8 Aberdeen West Sd From $59.98/nt   A 1 Star Hotel! 1 Star Hotel
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This Super 8 Motel is situated in the Hub City, approximately two miles from Northern State University, Wylie Park & Storybookland, and Dakota Prairie
 
Aberdeen Red Roof From $64.99/nt   A 2 Star Hotel! 2 Star Hotel
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Red Roof Aberdeen is located approximately three miles northwest of downtown Aberdeen, two miles from the Cal Ripkin Stadium & Museum, and 40 miles from
We have over 400 properties in the Chestertown, Maryland area.
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