Lodging and Vacation Rentals in Chestertown Maryland

Banning House is a beautifully restored single family home in the heart of historic Chestertown up the street from The Chester River. You can walk to everything or simply sit outside on your front porch and enjoy the neighborhood.

Upstairs over the store in downtown Chestertown.

Discover a historic and award-winning bed and breakfast in Chestertown, MD. This romantic inn is situated on 35 beautiful acres with glorious views and delicious breakfasts! Unforgettable rooms offer whirlpool tubs, fireplaces, and flat-screen TVs.

Magnificent 1000 acre estate just 5 miles outside Chestertown. Contemporary style 6 br home sited perfectly high above the river, ideal for fishing and kayaking, wonderful views of the sun setting over the water. House has fully equipped kitchen–

This simple, water-front cottage is 10 miles outside of Chestertown on the Chester River. It has 3 bedrooms, 2 baths, a wood-burning fireplace and a fully equipped kitchen.

54 Unit Apartments - Built 1967. All two bedroom, 1 bath with laundry facility. Wall to wall carpet and central air conditioning. Managed by Lee Davis

Elegant 12 room waterfront manor house with enchanting sunsets over the Chesapeake Bay on Maryland's Eastern Shore.

This comfortable quiet cottage is just a mile outside of historic Chestertown. It has two bedrooms and one bath and comes complete with linens and a fully equipped kitchen.

Modern convenience with 81 rooms. Close to Chestertown's Historic District. Breakfast is complimentary.

Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.

Gothic Revival Victorian, fully restored. Full breakfast and afternoon tea. Within blocks of the Historic District of Chestertown.

A country estate located within 5 miles of Chestertown on the Jarrett Creek.

A screened porch which is steps from the dock that hosts two kayaks for guests use and a simple floating dock for entry/exit.

28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.

Modern conveniences with 53 rooms. Close to Chestertown's Historic District.

With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination.

Spend a night – or a weekend – in charm and comfort. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its

This countryside property with wildlife pond and woodside fields, includes a two-story historic house and barn. Ideal for romantic get-a-ways, retreats, hunting parties or a country wedding.

Two allergy-friendly rooms in a cozy 1947 Cape Cod - a minute's walk from Washington College. "The soul should always stand ajar," [ready to welcome] - Emily Dickinson

This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.

We are minutes from Washington College, the 10th oldest college in the United States. Highlight your stay with the fine dining and tapas bar menu at The Kitchen at The Imperial.

Impeccably restored 18th century tavern. "Afternoon tea served daily.

Victorian gem located in Chestertown's Historic District