Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Chestertown Romantic Hotels

Aerial view
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 SAR 480
SAR 665 total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1890)
"Excellent hotel Really nice staff Love the valet guys "
United States
ben
Historic Inns of Annapolis
Front of property - evening/night
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 SAR 690
SAR 861 total
includes taxes & fees
8 Dec - 9 Dec
The Inn at Chesapeake Bay Beach Club
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
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
Property amenity
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, (699)
"The staff was wonderful."
United States
Pamela
The price is SAR 436
SAR 512 total
includes taxes & fees
22 Dec - 23 Dec
Courtyard by Marriott Baltimore Downtown/McHenry Row
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (878)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is SAR 667
SAR 760 total
includes taxes & fees
14 Dec - 15 Dec
Annapolis Waterfront Hotel, Autograph Collection
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (30)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Marina
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 SAR 221
SAR 763 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Fells Point Gem / In The Heart of Fells Point
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1002)
"Yes I love how the room was, I had an amazing stay, the staff was nice and easy to manage I loved it thank you "
United States
Carmen
The price is SAR 334
SAR 392 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Hotel & Conference Center
View from room
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 SAR 547
SAR 717 total
includes taxes & fees
28 Dec - 29 Dec
The Inn at Henderson's Wharf, an Ascend Collection Hotel
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Excellent hotel Really nice staff Love the valet guys "
ben 1-night trip
Posted 5 days ago
Historic Inns of Annapolis

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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.