Chestertown Hotels
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Our top choices for Chestertown hotels
The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
7.8 out of 10, Good, (83 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
Nicola
The price is €130
includes taxes & fees
2 Jun - 3 Jun
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (449 reviews)
"Nothing special but good for the price. "
Andreas
The price is €69
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (914 reviews)
"Great visit"
Danielle
The price is €102
includes taxes & fees
30 Jun - 1 Jul
Driftwood Inn
Driftwood InnChestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
Gabriel
The price is €60
includes taxes & fees
1 Jun - 2 Jun
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (913 reviews)
"Room was clean and staff took very good care of us"
Carol
The price is €101
includes taxes & fees
1 Jun - 2 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Havre De Grace Aberdeen AreaHavre De Grace
6.6 out of 10, (992 reviews)
"Cold air dark room great staff!"
Marc
The price is €53
includes taxes & fees
2 Jun - 3 Jun
Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (141 reviews)
"We loved the quaintness of the room, complete with a gas fireplace and floor to ceiling drapes. Having a restaurant right on site was incredible. I especially loved the girl dinner deal! We enjoyed the stay and the property was beautiful."
Kiana
The price is €176
includes taxes & fees
1 Jun - 2 Jun
Relax Inn Smyrna Dover Coastal Gateway
Relax Inn Smyrna Dover Coastal GatewaySmyrna
7.8 out of 10, Good, (98 reviews)
"I was in town for just one night and ended up booking this last minute. I’ve never stayed at a motel before because of the stigma, but I was pleasantly surprised. Everything was very clean, and the owner at the front desk was extremely friendly and welcoming. A nice bonus was the smart TV, which let me log into my own accounts and relax. Overall, a great experience and definitely changed my perspective on motels."
Michael
The price is €87
includes taxes & fees
1 Jun - 2 Jun
Vandiver Inn
Vandiver InnHavre De Grace
9.4 out of 10, Exceptional, (547 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
Shannon
The price is €139
includes taxes & fees
1 Jun - 2 Jun
Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and the owner was very helpful will definitely stay there again"
John
The price is €133
includes taxes & fees
2 Jun - 3 Jun
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
Sandra
The price is €170
includes taxes & fees
4 Jun - 5 Jun
Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very good, (1,005 reviews)
"Good hotel for the price"
Brenda
The price is €110
includes taxes & fees
8 Jun - 9 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APGAberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
"Great place to stay"
Harry
The price is €85
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location and very clean!"
Neille
The price is €132
includes taxes & fees
24 Jun - 25 Jun
Quality Inn Smyrna
Quality Inn SmyrnaSmyrna
7.6 out of 10, Good, (1,003 reviews)
"The rooms were clean and the staff was very kind and helpful. Overall, it was a great value for us!"
Jesse
The price is €83
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/AberdeenAberdeen
9.0 out of 10, Wonderful, (660 reviews)
"Clean, comfortable, decent breakfast."
Diane
The price is €91
includes taxes & fees
8 Jun - 9 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
8.8 out of 10, Excellent, (378 reviews)
"Great stay at this"
Wilson
The price is €94
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
9.4 out of 10, Exceptional, (1,003 reviews)
"Best place to stay"
Victor
The price is €86
includes taxes & fees
7 Jun - 8 Jun
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MDAberdeen
7.0 out of 10, Good, (873 reviews)
"Breakfast could be better. "
Joseph V
The price is €52
includes taxes & fees
7 Jun - 8 Jun
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (1,853 reviews)
"Great hotel..will definitely be back"
Randy
The price is €143
includes taxes & fees
8 Jun - 9 Jun
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.
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Stay near popular Chestertown attractions
Learn more about Chestertown
Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.
More cheap stays in Chestertown
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
The price is €59 per night from 7 Jun to 8 Jun
€59
7 Jun - 8 Jun
includes taxes & fees
7.4/10 Good! (1,123 reviews)
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- Visit Cedonia
- Visit Dundalk Marine Terminal
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