Travel & Accomodations

Hotel

Comfort Inn & Suites Chestertown

To book, please click the link below. You may also call reservations at 410-778-0778 and mention the Cassidy-Hitt wedding to get the room block rate. The cut-off date to secure our discounted rate is August 15, 2026. Transportation will be provided to and from Clovelly.

Hotel

The Brampton Inn

Hotel

The River Inn

The Inn is conveniently located just around the corner from Clovelly - 10‑minute walk or a 2‑minute drive

House Or Rental

Airbnb - Owl Cottage

4 guests · 1 bedroom · 2 beds · 1 bath Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Charming Haven on High

4 guests · 2 bedrooms · 3 beds · 1.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Pole Pole House

4 guests · 2 bedrooms · 3 beds · 1 bath Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - 114 High Upper

4 guests · 2 beds · 1 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - 114 High Lower

4 guests · 2 beds · 1 bath Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Church Alley

4 guests · 2 beds · 1.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Historic High Street House

4 guests · 3 beds · 2.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - High Tide & Hound

5 guests · 3 beds · 2 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Bright & New Chestertown

4 guests · 2 bedrooms · 2 beds · 1 bath Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Magnolia House

6 guests · 4 beds · 3.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Loft at Fountain Park

8 guests · 4 bedrooms · 5 beds · 2.5 baths Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Church Alley

6 guests · 2 bedrooms · 2 beds · 1.5 baths Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Historic Chestertown

5 guests · 3 bedrooms · 3 beds · 2.5 bath Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Shabby Chic

4 guests · 2 beds · 2 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Primrose Cottage

6 guests · 3 bedrooms · 4 beds · 1 bath Downtown Shuttle Pickup and drop off available Walkable to Welcome Party

House Or Rental

Airbnb - Cozy Chestertown

6 guests · 3 beds · 2 baths Downtown shuttle pick‑up and drop‑off available

House Or Rental

Airbnb - Classic Victorian

8 guests · 8 beds · 2.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Chesapeake Getaway

7 guests · 4 beds · 2 baths 25-minute drive to Clovelly

House Or Rental

Vrbo - Historic Retreat

6 guests · 3 beds · 2 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Vrbo - Heart of Chestertown Apartment

4 guests · 2 beds · 1 bath Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Vrbo - Downtown Waterfront

8 guests · 5 beds · 3 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Vrbo - The Portside Manor

8 guests · 4 beds · 3 baths Downtown shuttle pick‑up and drop‑off Walkable to Welcome Party

House Or Rental

Airbnb - Down by the River

10 guests · 5 beds · 2.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Vrbo - Country Estate

10 guests · 6 beds · 3.5 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Vrbo - Circa 1900

10 guests · 4 beds · 2 baths Downtown shuttle pick‑up and drop‑off available Walkable to Welcome Party

House Or Rental

Airbnb - Harbour View Haven

10 guests · 6 beds · 2 baths 10-minute drive to Clovelly Please reach out to Brielle so we can coordinate shuttle pick‑up and drop‑off