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Search Romantic Hotels in Chestertown

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Top Chestertown Romantic Hotels

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Recommended hotels in Chestertown

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (59)
"Great place to get some quiet rest by the water"
The price is 3.469.038 ₫
3.850.633 ₫ total
includes taxes & fees
12 Aug - 13 Aug
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (791)
"It was a clean comfortable spot to rest for the night. "
The price is 2.875.133 ₫
3.191.398 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (384)
"Good location."
The price is 1.887.912 ₫
2.095.583 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property – evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (172)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is 1.665.034 ₫
1.848.319 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Driftwood Inn
Quality Inn
Free daily self-service breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1005)
"Wonerful place, all good..Hotel,area, staff."
The price is 2.342.584 ₫
2.600.268 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Quality Inn
Relax Inn Smyrna
Reception

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is 2.336.291 ₫
2.598.891 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Relax Inn Smyrna
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (819)
"Front desk service was exceptional!!"
The price is 2.875.133 ₫
3.191.397 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Hampton Inn Middletown
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (599)
"Easy to navigate and nice, helpful staff "
The price is 3.041.636 ₫
3.376.216 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express & Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (257)
"Nice place to stay"
The price is 2.936.752 ₫
3.259.794 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites by Marriott Middletown
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

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 Garfield Center for the Arts at the Prince Theater. 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.
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 Garfield Center for the Arts at the Prince Theater 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.