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Romantic Hotels & Resorts in Chestertown from AU$243

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Check availability on Chestertown Romantic Hotels

Best Chestertown Romantic Hotels

Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (115)
"Great INN super nice staff"
United States
Eric
The price is AU$377
includes taxes & fees
23 Oct - 24 Oct
Kent Island Resort
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1872)
"The hotel was absolutely clean and close to the shops and restaurants. "
United States
Trudy
Historic Inns of Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (422)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is AU$371
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
Marina
Cozy Fells Point Gem / In The Heart of Fells Point
Cozy Fells Point Gem / In The Heart of Fells Point
9.8 out of 10, Exceptional, (198)
"Great place all around "
United States
Sophia F.
The price is AU$318
includes taxes & fees
27 Oct - 28 Oct
Cozy Fells Point Gem / In The Heart of Fells Point
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"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
Property amenity
Courtyard by Marriott Baltimore Downtown/McHenry Row
Courtyard by Marriott Baltimore Downtown/McHenry Row
3.0 star property
9.0 out of 10, Wonderful, (680)
"Great location "
United States
Kimberley
The price is AU$243
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Baltimore Downtown/McHenry Row
Room, 2 Queen Beds, Non Smoking, Balcony
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (872)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is AU$357
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph Collection
View from room
The Inn at Henderson's Wharf, an Ascend Collection Hotel
The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
9.2 out of 10, Wonderful, (744)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is AU$319
includes taxes & fees
9 Nov - 10 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (146)
" The location and the house! Great communication from owner!! Thank you!!"
United States
steve j.
The price is AU$936
includes taxes & fees
23 Oct - 24 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Fridge, microwave, oven, stovetop
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
9.8 out of 10, Exceptional, (64)
"Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips."
United States
Anonymous traveller
The price is AU$438
includes taxes & fees
29 Oct - 30 Oct
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
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.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Loved everything. Perfect location right on the main drag "
Timothy 1-night trip
Posted 3 days ago
Historic Inns of Annapolis

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 Chesapeake Bay. 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.
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 Chesapeake Bay 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.