Chesapeake Bay Vacation Rentals

Chesapeake Bay Vacation Rentals

Vacation Home Rentals

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Hotels and Bed and Breakfasts are nice, but sometimes you want the room, freedom and amenities that a vacation home provides.

We are happy to provide a selection of Chesapeake Bay region homes available as vacation rentals.

A vacation rental house may be the perfect option for family gatherings, reunions, or just a quiet getaway.  Take a look at the different options available. Some are large, with lots of bedrooms, and well-suited to large gatherings. Others are cozy cottages, best for couples or small families.

Many of the vacation rentals available are waterfront, while others have convenient downtown locations. We’ve listed a lot of properties here, but there are still more available.

If you don’t see what you’re looking for on our list, check the complete vacation rental listings at VRBO and TripAdvisor. You’re sure to find something that suits your needs.

If prices are a little too high for your budget, consider scheduling your vacation off the peak season. Spring and fall are beautiful times of year in the Chesapeake Bay region and some of the home owners offer lower rates outside the summer season. Another money-saving option is to look for newly listed homes, which often have discounted rates. See newly listed vacation rentals at VRBO. com.

Annapolis MD

Maryland’s historic waterfront Capital city.

Historic Annapolis Home with Off-Street Parking – Three bedroom townhouse located adjacent to the Paca Gardens and the Naval Academy. Has large bonus room for additional guests. Custom kitchen, rooftop deck. 

Eastport Rental – Newly renovated home in the Eastport neighborhood of Annapolis. Three bedroom and 3.5 baths. Private swimming pool in a completely fenced back yard. 

The Constellation House – Located close to City Dock and the Naval Academy. 1900’s duplex with three bedrooms and 2.5 baths.

Anchors Aweigh – Four bedroom, 2.5 bath historic home located less than a block from the William Paca House and Garden and within walking distance of City Dock, the Naval Academy, and downtown shops and restaurants.

Three-Story Three Bedroom Home Near State House – This renovated historic district home is located close to the State House. Three bedrooms, 3.5 baths. Has driveway parking.

More Annapolis Vacation Home Rentals – Choose from additional available rentals.

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Cambridge MD

Historic Eastern Shore town on the shores of the Choptank River.

Waterfront Home in Cambridge, Maryland – Four bedroom 1.5 bath bungalow on the Choptank River, with waterfront deck.

Waterfront Cambridge Home with Beach, Dock & Pool – Three bedroom, 2 bath home on the Choptank River.

More Cambridge Vacation Rentals – Choose from additional available rentals.


Cape Charles VA

Located at the southern end of Virginia’s Eastern Shore, Cape Charles has an in-town beach, shops, restaurants, marinas, and golf courses.

Bay Cottage – Three bedroom, 1.5 bath home located near Cape Charles beach. Large screened porch with Chesapeake Bay views.

One Bedroom Suite in Downtown Cape Charles – Modern loft style apartment located in a historic building. Close to downtown shops and restaurants and two blocks from Cape Charles beach.

Hummingbird Cottage – Two bedroom, 2 bath craftsman style home located across from Central Park.

More Cape Charles Area Vacation Rentals – Choose from additional available rentals.


Crisfield MD

Eastern Shore town known for blue crabs, boating, and fishing.

Waterfront Crisfield Condo – Top floor corner unit (5th floor). Three bedrooms, 2 baths. Comes with a 40 foot boat slip.

Three Bedroom Condo – Waterfront condo with water views from balcony and screened porch. Swimming pool on site.

Two Bedroom Condo Overlooking Somer’s Cove – Two bedroom, two bath waterfront condo at Captain’s Galley.

More Crisfield Vacation Rentals – Choose from additional available rentals.


North Beach MD

Western Shore town with a popular beach and boardwalk on the Chesapeake Bay.

South Winds Condo – Two bedroom, 2 bath fourth floor condo overlooking the Chesapeake Bay.

Three Bedroom Cottage – Three bedroom, 2 bath home, located within walking distance of North Beach boardwalk.

Five Bedroom Bayfront Home – Five bedroom, five bath home located on the Chesapeake Bay. Large rooftop deck with open and covered areas.

More North Beach Vacation Rentals – Choose from additional available rentals.


Northern Neck of VA

The Northern Neck of Virginia’s Western Shore offers nature, history, relaxation, and miles of waterfront property.

Colonial Beach 5 Bedroom Home – Five bedroom, 3 bath home with large screened porch. Located close to boardwalk and beach.

Colonial Beach Waterfront Cottage – Two bedroom, two bath fisherman’s cottage on the Potamac River.

Three Bedroom Waterfront Home on the Yecomoco River – Three bedrooms, 2 baths. Has dock.

Reedville Area Waterfront Home – Four bedrooms, 1.5 baths. Located on a cove with private dock.

Four Bedroom Home with Private Beach – Four bedroom, 4.5 bath waterfront home located where the Rappahannock meets the Chesapeake Bay.

More Northern Neck Vacation Rentals – Choose from additional available rentals.

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Oxford MD

Eastern Shore waterfront town on the Tred Avon River. Home of the Oxford-Bellvue Ferry and many marinas and boatyards.

Oxford Cottage – Four bedroom, 2 full, 2 half bath home located in the town of Oxford, Maryland

Beachfront Oxford Home – Three bedroom, 2.5 bath located in town, adjacent a beach on the Tred Avon River.

More Oxford Vacation Rentals – Choose from additional available rental homes.


Solomons Island MD

Popular boating destination and weekend getaway located on the Patuxent River. Calvert Marine Museum, Annmarie Gardens and Sculpture Park, and Calvert Cliffs State Park are all located nearby.

Waterfront Home on Solomons Island – Four bedroom, 5.5 bath waterfront home located within walking distance of shops and restaurants.

Waterfront Home in Dowell, Maryland – This five bedroom, 5 bath waterfront home is located in Dowell, a short drive to Solomons Island.

More Solomons Island Area Vacation Rentals – Choose from additional available rentals in the Solomons Island area.


St Michaels MD

This Eastern Shore town is popular with boaters and travelers. Home of the Chesapeake Bay Maritime Museum.

In-Town Historic Home on the Harbor – Six bedroom, 3.5 bath home located on the harbor, in the center of the town of St. Michaels.

Two Bedroom St. Michaels Cottage – Two bedroom, 1.5 bath in-town cottage located within walking distance of museums, shops, and restaurants.

Three Bedroom St. Michaels Cottage – Three bedroom, 3, bath renovated cottage located in town.

“Dollhouse” in Central St. Michaels – Two bedroom, 1.5 bath two-story historic home located in town.

More St. Michaels Vacation Rentals – Choose from additional available rentals in St. Michaels and nearby.


Tilghman Island MD

Eastern Shore waterman’s town on the Chesapeake Bay.

Tilghman Island Cottage – Three bedroom, 2 bath cottage located close to Knapps Narrows.

Three Bedroom Home on the Chesapeake Bay – Three bedroom, 3 bath waterfront Tilghman Island cottage.

Waterfront Home on the Chesapeake Bay – Three bedroom, 3 bath home.

More Tilghman Island Area Vacation Rentals – Choose from additional available vacation rentals in Tilghman and the surround area.


More Chesapeake Bay Vacation Rentals

Chestertown MD –  Colonial Beach VA – Deal Island MD – Deale MD – Gloucester VA – Lancaster VA – Reedville VA – St Leonard MD – North East MD – White Stone Beach VA