Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (535 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
"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
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (436 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is NT$4,898
NT$6,236 total
includes taxes & fees
Feb 16 - Feb 17
The Inn at Chesapeake Bay Beach Club
Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (901 reviews)
"Great location, nice and clean "
United States
Micah
The price is NT$6,381
NT$7,274 total
includes taxes & fees
Mar 1 - Mar 2
Annapolis Waterfront Hotel, Autograph Collection
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,877 reviews)
"Great rooms, very clean, loved our stay "
United States
Matthew
Historic Inns of Annapolis
Exterior

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
Locust Point
9.0 out of 10, Wonderful, (725 reviews)
"Great clean hotel"
United States
Robert
The price is NT$3,929
NT$4,617 total
includes taxes & fees
Mar 1 - Mar 2
Courtyard by Marriott Baltimore Downtown/McHenry Row
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.
View all properties

Top Chestertown Hotel Reviews

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

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

10/10 Excellent
"It was quiet and very clean‼️"
Tammy 2-night trip
Posted 3 days 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 vacation? You might consider checking out some of the nearby sights and attractions such as Northern Chesapeake Bay, Chesapeake Bay, or Historical Society of Kent County Maryland. 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 Northern Chesapeake Bay, Chesapeake Bay, or Historical Society of Kent County Maryland 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.

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