Chestertown hotels from RM258
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18 Aug - 19 AugTomorrow
19 Aug - 20 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
RM423
RM470 total
includes taxes & fees
13 Sept - 14 Sept
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
Linda
RM256
RM284 total
includes taxes & fees
25 Aug - 26 Aug
3. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
Lynda
RM438
RM501 total
includes taxes & fees
14 Sept - 15 Sept
4. Driftwood Inn
Driftwood InnChestertown
Daryl
RM258
RM286 total
includes taxes & fees
23 Aug - 24 Aug
5. Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
John
RM510
RM566 total
includes taxes & fees
1 Sept - 2 Sept
6. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
Myrna
RM733
RM813 total
includes taxes & fees
7 Sept - 8 Sept
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
RM396
RM444 total
includes taxes & fees
30 Aug - 31 Aug
10. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
walter
RM340
RM380 total
includes taxes & fees
30 Aug - 31 Aug
11. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
Albert
RM363
RM406 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
RM359
RM402 total
includes taxes & fees
25 Aug - 26 Aug
13. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
Jonathan
RM406
RM451 total
includes taxes & fees
8 Sept - 9 Sept
14. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
Karen
RM678
RM753 total
includes taxes & fees
8 Sept - 9 Sept
15. SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle River
Jennifer
RM435
RM502 total
includes taxes & fees
3 Sept - 4 Sept
16. Vandiver Inn
Vandiver InnHavre De Grace
Joan
RM652
RM730 total
includes taxes & fees
13 Sept - 14 Sept
17. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
James
RM483
RM536 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
RM357
RM400 total
includes taxes & fees
1 Sept - 2 Sept
19. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
chanel
RM489
RM543 total
includes taxes & fees
24 Aug - 25 Aug
20. Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/AberdeenAberdeen
Anthony
RM383
RM429 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
The Lodge at Great Oak Landing
10/10 Excellent
"Great place to stay. Beautiful area."
Best Western Plus Hotel & Conference Center
10/10 Excellent
"Very nice staff at check-in and check-in was quick and easy. My particular room was large and very clean. There were plenty of towels too. I would stay again."
Best Western Kent Narrows Inn
10/10 Excellent
"My husband and I stayed overnight for a quick trip to get away for our anniversary. The gentleman who checked us in gave us a great recommendation for dinner. We used the hot tub and the sauna. Our room was a king size that looked out over the parking lot but towards the water which is what we wanted. We slept in so we didn't have breakfast but the menu that was put up looked amazing."
La Quinta Inn & Suites by Wyndham Aberdeen-APG
10/10 Excellent
"It was fine."
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
10/10 Excellent
"Nothing was bad the staff and the breakfast was great"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
8/10 Good
"Clean"
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"Five star hotel for me"
Comfort Inn & Suites Chestertown
8/10 Good
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didnโt. The cards worked well on the room doors but not on the entrance door. It was an inconvenience to walk around the building to get it the main entrance if the card did not work."
Red Roof Inn & Suites Chestertown
10/10 Excellent
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
More cheap stays in Chestertown
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
RM242
RM271 total
3 Sept - 4 Sept
includes taxes & fees
Hampton Inn & Suites Edgewood/Aberdeen-South
2110 Emmorton Park Rd Edgewood MD
RM340
RM380 total
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (1,006 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
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
RM434
RM510 total
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,001 reviews)
Holiday Inn Express White Marsh by IHG
10542 Philadelphia Road Perry Hall MD
RM447
RM516 total
17 Sept - 18 Sept
includes taxes & fees
