Chestertown hotels from RM259
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17 Aug - 18 AugTomorrow
18 Aug - 19 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur top choices for Chestertown hotels
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
Deanna
RM426
RM472 total
includes taxes & fees
13 Sept - 14 Sept
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
Linda
RM257
RM286 total
includes taxes & fees
24 Aug - 25 Aug
3. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
Lynda
RM439
RM501 total
includes taxes & fees
1 Sept - 2 Sept
4. Driftwood Inn
Driftwood InnChestertown
Daryl
RM258
RM286 total
includes taxes & fees
19 Aug - 20 Aug
5. Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
John
RM510
RM566 total
includes taxes & fees
26 Aug - 27 Aug
6. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
Myrna
RM733
RM813 total
includes taxes & fees
19 Aug - 20 Aug
7. Fairfield Inn & Suites by Marriott Aberdeen
Fairfield Inn & Suites by Marriott AberdeenAberdeen
Marie
RM449
RM503 total
includes taxes & fees
14 Sept - 15 Sept
8. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
Jackie
RM516
RM572 total
includes taxes & fees
1 Sept - 2 Sept
9. Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
Mark
RM399
RM447 total
includes taxes & fees
30 Aug - 31 Aug
10. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
walter
RM343
RM384 total
includes taxes & fees
8 Sept - 9 Sept
11. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
Albert
RM364
RM408 total
includes taxes & fees
7 Sept - 8 Sept
12. La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APGAberdeen
Niall
RM361
RM405 total
includes taxes & fees
24 Aug - 25 Aug
13. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
Jonathan
RM409
RM454 total
includes taxes & fees
7 Sept - 8 Sept
14. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
Karen
RM682
RM757 total
includes taxes & fees
8 Sept - 9 Sept
15. SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle River
KaTerra
RM435
RM502 total
includes taxes & fees
3 Sept - 4 Sept
16. Vandiver Inn
Vandiver InnHavre De Grace
Joan
RM652
RM730 total
includes taxes & fees
19 Aug - 20 Aug
17. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
James
RM486
RM540 total
includes taxes & fees
30 Aug - 31 Aug
18. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHGEdgewood
Chelsea
RM360
RM403 total
includes taxes & fees
1 Sept - 2 Sept
19. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
chanel
RM493
RM547 total
includes taxes & fees
24 Aug - 25 Aug
20. Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/AberdeenAberdeen
Anthony
RM385
RM432 total
includes taxes & fees
27 Aug - 28 Aug
Stay near popular Chestertown attractions
Washington College
8.6/10 (87 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
Chestertown Historic District
This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick pavements along the Chester River or visit during the annual Tea Party Festival reenactments.
Garfield Center for the Arts at the Prince Theater
6.8/10 (5 reviews)
This historic 1928 theatre offers an intimate setting for plays, music, and lectures in city centre Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.
River Arts Chestertown
7.4/10 (6 reviews)
Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
Wilmer Park
8.2/10 (13 reviews)
Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
Kings Town Park
Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.
Crumpton Auction
8.8/10 (3 reviews)
Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.
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.
See all hotels in Chestertown
Top Chestertown Hotel Reviews
Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
"Best place to stay on the harbor close to downtown. Great dock area with drinks and dining. Wonderful experience โญ"
Historic Inns of Annapolis
10/10 Excellent
"The location is perfect! Great view from our room and close to everything. The hotel is historic which gives it a lot of charm. We really enjoyed our stay. The room was clean and comfortable."
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
10/10 Excellent
"Everything about our stay was great"
Best Western Kent Narrows Inn
8/10 Good
"The property needs updating"
Best Western Plus Hotel & Conference Center
10/10 Excellent
"Shuttle to medical center was great. Food was good for breakfast and to our surprise there was also dinner provided. Great place to stay."
The Lodge at Great Oak Landing
8/10 Good
"The room was clean and comfortable and the staff was great. Things to note are that there is no restaurant on the premises or even close by, and the cell phone reception was quite poor. The setting is beautiful, though, so if you are there to just relax by the pool, you will be quite happy"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
10/10 Excellent
"Great place to stay. Staff was very nice, courteous, helpful, and the hotel was clean, nice."
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"The rooms and the entire hotel are well maintained and very clean. The staff is very nice and accommodating. We always stay here when we need accommodations in the area! A wonderful experience every stay!"
La Quinta Inn & Suites by Wyndham Aberdeen-APG
8/10 Good
"staff allowed early check in!!"
More cheap stays in Chestertown
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
RM243
RM272 total
3 Sept - 4 Sept
includes taxes & fees
Hampton Inn & Suites Edgewood/Aberdeen-South
2110 Emmorton Park Rd Edgewood MD
RM343
RM384 total
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
WoodSpring Suites Baltimore White Marsh - Nottingham
4985 Mercantile Road Baltimore MD
RM341
RM394 total
20 Aug - 21 Aug
includes taxes & fees
5.6/10 (1,002 reviews)
SpringHill Suites Baltimore White Marsh/Middle River
6110 Greenleigh Avenue Middle River MD
RM435
RM502 total
3 Sept - 4 Sept
includes taxes & fees
9/10 Wonderful! (905 reviews)
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
RM436
RM513 total
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,011 reviews)
Holiday Inn Express White Marsh by IHG
10542 Philadelphia Road Perry Hall MD
RM447
RM516 total
17 Sept - 18 Sept
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
