Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Top Chestertown Romantic Hotels

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (125)
"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 NT$3,905
NT$5,426 total
includes taxes & fees
Dec 1 - Dec 2
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (427)
"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 NT$5,730
NT$7,153 total
includes taxes & fees
Dec 1 - Dec 2
The Inn at Chesapeake Bay Beach Club

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

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1896)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (876)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is NT$4,565
NT$5,204 total
includes taxes & fees
Dec 18 - Dec 19
Annapolis Waterfront Hotel, Autograph Collection

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (29)
"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

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
Locust Point
9.0 out of 10, Wonderful, (694)
"Parking was easy. The property is very nice and the personel very friendly."
United States
Katia
The price is NT$4,179
NT$4,911 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott Baltimore Downtown/McHenry Row

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

3.0 star property
Fells Point
9.2 out of 10, Wonderful, (750)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is NT$4,460
NT$5,861 total
includes taxes & fees
Nov 25 - Nov 26
The Inn at Henderson's Wharf, an Ascend Collection Hotel

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1001)
"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 NT$3,606
NT$4,237 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Hotel & Conference Center
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.

Top Chestertown Hotel Reviews

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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.