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Find Romantic Hotels in Chestertown from S$167

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Check availability on Chestertown Romantic Hotels

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Top Romantic Hotels in Chestertown

Vandiver Inn
Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (502)
"Wonderful stay. Will stay here again!"
Vandiver Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (103)
"It's only 20 min from the downtown annapolis.Clean too."
The price is S$550
includes taxes & fees
8 Jul - 9 Jul
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (399)
"Staff was very polite and friendly. "
The price is S$336
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (835)
"Front desk staff was very friendly and helpful."
The price is S$312
includes taxes & fees
4 Aug - 5 Aug
Annapolis Waterfront Hotel, Autograph Collection
134 Prince - Luxury Boutique Hotel
Front of property

134 Prince - Luxury Boutique Hotel

2.5 star property
9.6 out of 10, Exceptional, (20)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1792)
"Wonderful stay!"
Historic Inns of Annapolis
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.

Frequently asked questions

Searching for romantic hotels in Chestertown?
Are you looking for a romantic getaway? You might consider checking out some of the nearby sights and attractions such as Historical Society of Kent County Maryland, Rolphs Wharf Marina or Chestertown Historic District. If you're interested in staying close to a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you'll be able to see everything on your list.
What's the best place to stay for a romantic getaway to Chestertown?
Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking.
How many romantic hotels should we expect to find in Chestertown?
Expedia has 7 romantic Chestertown hotels for you both to enjoy.
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, take a look at these details about year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to do in Chestertown?
There's nothing better than wandering around a new place with your sweetheart, so consider checking out all that Chestertown has to offer. A visit to Historical Society of Kent County Maryland, Rolphs Wharf Marina or Chestertown Historic District 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 centre. If you'd like to explore around the area, consider renting a car to explore more sights.