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Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chestertown Romantic Hotels

We don't have any properties that match your exact search

Recommended hotels in Chestertown

The Lodge at Great Oak Landing
Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (58)
"Great place to get some quiet rest by the water"
The price is NT$3,956
NT$4,391 total
includes taxes & fees
Aug 6 - Aug 7
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Welcome to our reception area, where friendly staff are available to assist with your stay.

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 NT$3,287
NT$3,648 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (384)
"Good location."
The price is NT$2,153
NT$2,389 total
includes taxes & fees
Aug 11 - Aug 12
Red Roof Inn & Suites Chestertown
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is NT$1,899
NT$2,108 total
includes taxes & fees
Aug 6 - Aug 7
Driftwood Inn
Quality Inn
Enjoy a sumptuous spread of fresh bread, pastries, and fruits at our buffet counter.

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Everyone very friendly "
The price is NT$2,718
NT$3,017 total
includes taxes & fees
Sep 4 - Sep 5
Quality Inn
Relax Inn Smyrna
Commercial building with a brick facade and flat roof, featuring an office entrance and a service entrance.

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is NT$2,395
NT$2,664 total
includes taxes & fees
Aug 11 - Aug 12
Relax Inn Smyrna
Hampton Inn Middletown
Guests can dine in comfort at this hotel's spacious dining area, surrounded by six chairs and a large window with sheer curtains.

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (818)
"Front desk service was exceptional!!"
The price is NT$3,278
NT$3,639 total
includes taxes & fees
Aug 14 - Aug 15
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Relax in our stylish lobby with a seating area, reception desk, and digital display.

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (598)
"Easy to navigate and nice, helpful staff "
The price is NT$3,468
NT$3,850 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Relax in this stylish living space with a large flat-screen TV, dining area, and comfortable sofa.

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is NT$3,468
NT$3,850 total
includes taxes & fees
Aug 24 - Aug 25
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

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Beautiful, professional establishment. "
Crispin 3-night trip
Posted 2 days ago
Sagamore Pendry Baltimore

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, 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 neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
What's the best hotel for couples in Chestertown?
Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking.
How many romantic hotels will we be able 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, 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, 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 center. If you'd like to explore around the area, consider renting a car to take in more sights.