An aerial view of a town with a river, buildings, and surrounding greenery.

Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Chestertown romantic hotels

Marina
Exterior detail
Coffee/tea maker, fridge, microwave, oven
Smart TV, DVD player

1. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
United States
Tammy
AED 191
AED 806 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Fells Point Gem / In The Heart of Fells Point
Property grounds
Interior
Coffee/tea maker, fridge, microwave, oven
Marina

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
United States
Buu T.
AED 1,322
AED 2,345 total
includes taxes & fees
31 Aug - 1 Sep
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Sun loungers, beach towels
Exterior
Smart TV, DVD player, books, video library
5 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
AED 1,200
AED 2,253 total
includes taxes & fees
31 Aug - 1 Sep
5-bedroom vacation home 5 minutes from historic Charlestown
Marina
Smart TV, books
Coffee/tea maker, fridge, microwave, oven
Smart TV, books

4. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Mary G.
AED 826
AED 1,650 total
includes taxes & fees
31 Aug - 1 Sep
Cozy 2br home w/ parking in downtown Annapolis
Exterior
Exterior detail
Interior
Exterior detail

5. Beautiful farm house on 500 acres of preserved farmland

Beautiful farm house on 500 acres of preserved farmland
Smyrna
United States
Tom L.
AED 4,591
AED 6,157 total
includes taxes & fees
19 Sep - 20 Sep
Beautiful farm house on 500 acres of preserved farmland
On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels
Interior
Interior

6. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
AED 3,122
AED 5,323 total
includes taxes & fees
7 Sep - 8 Sep
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Exterior
Dining
Exterior
Interior

7. Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
AED 3,122
AED 5,315 total
includes taxes & fees
31 Aug - 1 Sep
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"
Michele 2-night trip
Posted 3 days ago
Annapolis Waterfront Hotel, Autograph Collection

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 Chestertown Historic District, Northern Chesapeake Bay, or Chesapeake Bay. 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 Chestertown Historic District, Northern Chesapeake Bay, 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 center. If you'd like to explore around the area, consider renting a car to take in more sights.

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