Search Wedding Hotels in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Wedding Hotels

Our top choices for Chestertown wedding hotels

Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is 3.373.845 ₫
4.671.022 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Kent Island Resort
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1907)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
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
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is 4.846.538 ₫
6.050.306 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Property amenity
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, (700)
"The staff was wonderful."
United States
Pamela
The price is 3.060.628 ₫
3.596.237 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Courtyard by Marriott Baltimore Downtown/McHenry Row
Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top 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, (881)
"Great location, nice and clean "
United States
Micah
The price is 4.683.209 ₫
5.338.858 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Annapolis Waterfront Hotel, Autograph Collection
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1000)
"Clean room, great location, very friendly and helpful staff"
United States
Beverly
The price is 2.346.666 ₫
2.757.334 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Best Western Plus Hotel & Conference Center
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (30)
"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
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
Fells Point
9.2 out of 10, Wonderful, (751)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
The price is 4.012.196 ₫
5.239.093 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
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

Explore a world of travel with Expedia