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Search Romantic Hotels in Chestertown

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Check availability on Chestertown Romantic Hotels

Tonight
30 Jul - 31 Jul
Tomorrow
31 Jul - 1 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Top Chestertown Romantic Hotels

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is Rp4.031.691
Rp4.803.356 total
includes taxes & fees
31 Jul - 1 Aug
Inn at Haven Harbour
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, (404)
"Staff was very polite and friendly. "
The price is Rp3.363.845
Rp4.151.313 total
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (105)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is Rp3.257.426
Rp4.236.959 total
includes taxes & fees
14 Aug - 15 Aug
Kent Island Resort
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1007)
"Great place to stay highly recommend it "
The price is Rp1.798.076
Rp2.076.779 total
includes taxes & fees
3 Aug - 4 Aug
Hilton Garden Inn Baltimore/White Marsh
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1832)
"Loved the hotel-great location "
Historic Inns of Annapolis
134 Prince - Luxury Boutique Hotel
Exterior

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
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1000)
"Convenient location"
The price is Rp1.820.331
Rp2.138.889 total
includes taxes & fees
17 Aug - 18 Aug
Best Western Plus Hotel & Conference Center
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | 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, (847)
"Front desk staff was very friendly and helpful."
The price is Rp3.751.918
Rp4.277.187 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Henderson's Wharf, Ascend Hotel Collection
View from room

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (699)
"Second time staying here - absolutely lovely. "
The price is Rp2.333.997
Rp3.068.091 total
includes taxes & fees
17 Aug - 18 Aug
The Inn at Henderson's Wharf, Ascend Hotel Collection
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Friendly and accommodating they really didn’t try to help out"
David Brian 1-night trip
Posted 8 days ago
Hampton Inn Baltimore/Glen Burnie
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"Great price and excellent service "
Reba 5-night trip
Posted 3 weeks ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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.
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 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.