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Find Romantic Hotels in Chestertown, MD

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Check availability on Chestertown Romantic Hotels

Tonight
2 Sep - 3 Sep
Tomorrow
3 Sep - 4 Sep
This weekend
5 Sep - 7 Sep
Next weekend
12 Sep - 14 Sep

Top Chestertown Romantic Hotels

Our top choices for Chestertown romantic hotels

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, (417)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is AED 826
AED 1,011 total
includes taxes & fees
1 Oct - 2 Oct
The Inn at Chesapeake Bay Beach Club
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1849)
"Excellent location, clean, friendly staff"
Historic Inns of Annapolis
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"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, (1001)
"Nice hotel "
The price is AED 392
AED 461 total
includes taxes & fees
7 Sep - 8 Sep
Best Western Plus Hotel & Conference Center
The Inn at Henderson's Wharf, an Ascend Collection Hotel
View from room

The Inn at Henderson's Wharf, an Ascend Collection Hotel

3.0 star property
9.2 out of 10, Wonderful, (719)
"Location is excellent rooms are really nice. Very good value. Staff very friendly have stayed here before and we will continue to book here when in Bmore"
The price is AED 571
AED 744 total
includes taxes & fees
1 Oct - 2 Oct
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Cozy Fells Point Gem / In The Heart of Fells Point
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

9.8 out of 10, Exceptional, (194)
"Great place close to eveything"
The price is AED 228
AED 751 total
includes taxes & fees
3 Sep - 4 Sep
Cozy Fells Point Gem / In The Heart of Fells Point
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (859)
"Easy check in, clean and close to everything "
The price is AED 871
AED 993 total
includes taxes & fees
28 Sep - 29 Sep
Annapolis Waterfront Hotel, Autograph Collection
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is AED 569
AED 1,319 total
includes taxes & fees
9 Sep - 10 Sep
Cozy 2br home w/ parking in downtown Annapolis
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Fridge, microwave, oven, stovetop

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."
The price is AED 562
AED 1,069 total
includes taxes & fees
9 Sep - 10 Sep
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.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location - easy to walk to most anywhere. Parking a bit expensive but overall experience was great "
Jason 2-night trip
Posted 1 day ago
Historic Inns of Annapolis
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Great everything. Staff, location. Need to go back when the pool is open!"
Cheryl 3-night trip
Posted 8 days ago
Sagamore Pendry Baltimore

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