Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is AED 526
AED 715 total
includes taxes & fees
15 Dec - 16 Dec
Kent Island Resort
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is AED 675
AED 843 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
Meeting facility
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Exterior detail
Vandiver Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is AED 652
AED 744 total
includes taxes & fees
17 Dec - 18 Dec
Annapolis Waterfront Hotel, Autograph Collection
Exterior
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
Locust Point
9.0 out of 10, Wonderful, (701)
"The staff was wonderful."
United States
Pamela
The price is AED 426
AED 501 total
includes taxes & fees
22 Dec - 23 Dec
Courtyard by Marriott Baltimore Downtown/McHenry Row
Exterior
The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
Fells Point
9.2 out of 10, Wonderful, (751)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is AED 559
AED 730 total
includes taxes & fees
2 Jan - 3 January 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center
2.5 star property
Medford
7.8 out of 10, Good, (1001)
"Clean room, great location, very friendly and helpful staff"
United States
Beverly
The price is AED 327
AED 384 total
includes taxes & fees
21 Dec - 22 Dec
Best Western Plus Hotel & Conference Center
Marina
Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (200)
"Great place all around "
United States
Sophia F.
The price is AED 202
AED 725 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Fells Point Gem / In The Heart of Fells Point
Exterior
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Canton
9.8 out of 10, Exceptional, (65)
"Brandon was a thoughtful host and responded quickly. The property was lovely and so convenient. "
United States
andrea s.
The price is AED 488
AED 1,056 total
includes taxes & fees
18 Dec - 19 Dec
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
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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Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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Frequently asked questions

Searching for romantic hotels in Chestertown?
Are you looking for a romantic vacation? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Chestertown Historic District, or Rolphs Wharf Marina. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chestertown?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to do in Chestertown?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Chestertown has to offer. A visit to Historical Society of Kent County Maryland, Chestertown Historic District, or Rolphs Wharf Marina might be just the ticket when you're checking out the sights.
What's the best way to get to Chestertown and around town during my romantic getaway?
These transportation options in Chestertown might help your romantic getaway go off without a hitch: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), which is the closest major airport, located 20.3 mi (32.7 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.