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peonies

Travel

The Wedding Website of Alicia Campbell and Gregory Mullikin
Make a weekend of it! Chestertown is one of Maryland's hidden gems, and we hope you'll enjoy exploring while you're here. Looking for lodging? Check Airbnb and VRBO for charming waterfront homes, cozy cottages, and historic rentals throughout the area. Since Chestertown has just two hotels, we've included both below—including our discounted room block at the Comfort Inn & Suites—as well as a few local bed & breakfasts. We encourage you to book early, as lodging can book up quickly, especially on weekends. Be sure to visit our Things to Do page for some of our favorite local restaurants, attractions, wineries, and activities to enjoy during your stay. We hope you enjoy this special corner of the Eastern Shore as much as we do!

Hotel

Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD 21620
 

Approx. 11 minutes (4.4 miles) We've reserved a discounted room block for our guests under "Campbell-Mullikin." Please note that this hotel requires a two-night minimum stay. We encourage you to book early, as rooms are limited and the block may fill before the reservation deadline. Complimentary breakfast and convenient access to downtown.

Hotel

Brampton 1860

25227 Chestertown Road, Chestertown, MD 21620
 

Approx. 10 minutes (4.3 miles) Elegant manor house with luxurious rooms and private cottages.

Hotel

Great Oak Manor

10568 Cliff Road, Chestertown, MD 21620
 

Approx. 23 minutes (13 miles) Stunning waterfront inn overlooking Fairlee Creek and the Chesapeake Bay.

Hotel

Inn at Mitchell House

8796 Maryland Parkway, Chestertown, MD 21620
 

Approx. 21 minutes (13 miles) Beautiful country estate offering peaceful

Hotel

White Swan Tavern

231 High Street, Chestertown, MD 21620
 

Approx. 7 minutes (3.1 miles) Historic boutique inn located in the heart of charming downtown Chestertown.

Hotel

The Guesthouse Bed and Breakfast

114 Washington Avenue, Chestertown, MD 21620
 

Approx. 8 minutes (3.3 miles) Cozy, intimate stay within walking distance of downtown shops and restaurants.

Hotel

Red Roof Inn & Suites Chestertown

160 Scheeler Rd, Chestertown, MD
 4108100555

Located next door to the Comfort Inn & Suites and just a 10-minute drive from Piney Grove. Ideal for guests who prefer the flexibility of a one-night stay. Approx. 10 minutes (4.5 miles)