Chesapeake Bay Vacation Rentals

Chesapeake Bay Vacation Rentals

Vacation Home Rentals


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.

Annapolis MD

vr annapolis historic home

Historic Home in the Heart of Downtown Annapolis
This fully renovated home was constructed in 1832. Located one block from Main Street in downtown Annapolis.  Gourmet kitchen.  Three bedrooms. 2.5 baths.  Sleeps six comfortably, nine with couch and air mattress.  More Info

vr annapolis eastport

Eastport Rental
One block from Chart House and Ruth’s Chris Steakhouse.  Large kitchen, private backyard with pond and grill.  Rooftop deck with water view. Three bedrooms, 3.5 baths, convertible beds.  Sleeps ten.  More Info

Annapolis Cottage Near Navy Marine Corps Stadium
This one bedroom cottage is located within walking distance of the stadium and 1 1/2 miles from City Dock.

More Annapolis Vacation Home Rentals

Cambridge MD

vr cambridge new lux

New Luxury Waterfront Home
Located ten minutes from Cambridge.  This waterfront home has a dock, sandy beach, and heated swimming pool.  The interior is modern and roomy, with a large eat-in kitchen.  This is a large house, with six bedrooms and five baths.  Sleeps sixteen. Canoe and kayaks are available for your use.  More Information.

vr cambridge cottage

The Cottage
“The Cottage” at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window.  This home sits on 10 acres of land with 1,000 feet of shoreline.  You can fish and crab from the dock then relax on the wrap-around screened porch or take a soak in the hot tub.  More Information

Cape Charles VA


The Dryden House
Newly renovated home in the historic district. Located across the street from the beach and two blocks from downtown shops and restaurants. This is a three story home with wrap-around porches. Bay views from almost every room. Four bedroom and three baths. Large kitchen.  More info.


Bay Creek Resort Condo
This condo is located in the Bay Creek Resort, where there are two signature golf courses, a private beach, swimming pools, a marina, and dining. Three bedroom and two baths.  More info.


More Cape Charles Area Vacation Rentals

Crisfield MD

crisfield vr janes

Waterfront Condo overlooking Janes Island
Luxury waterfront condo with great views.  Close to pool.  Deck and screened porch.  Located in a family-friendly condo development.
More info

crisfield vr new 5

New Fifth Floor Condominium
Fireplace, gourmet kitchen, jetted tub and private screened porch off the master suite.  Nice sunset views. Located at the water, close to everything.  More info

North Beach MD

north beach vr waterfront quiet

Quiet Waterfront Family Getaway
This home sits right out on the edge of the water.  Great views from the second story deck.  Three bedrooms, one full bath.
More info

north beach vr waterfront ches bay

Waterfront House on the Chesapeake Bay
Unobstructed views of the Chesapeake Bay.  Two bedrooms, 2.5 baths.  Located just steps away from the boardwalk. Porches on two levels.
More info

More North Beach Vacation Rentals


Northern Neck of VA

northern neck lux

Chesapeake Bay Luxury Beachfront Retreat
Get away from it all on Henry’s Island, offering alluring privacy and breathtaking views of the Chesapeake Bay.  Four bedrooms, four baths. Private sandy beach.
More info

northern neck vr lancaster

Lancaster Vacation Rental Cottage
Waterfront home on the Rappahannock River with boating, crabbing, fishing, beautiful sunsets, bird watching.  Large house with five bedrooms, 2.5 baths.  100 foot dock. Two kayaks.  Outside shower.
More info

More Northern Neck of Virginia Vacation Rentals


Oxford MD

oxford vr historic

Historic Waterfront Estate Home
This very private waterfront estate has six bedrooms and five and half baths.  Gourmet kitchen, dock, private pool, billiard room, outdoor grill. More info 

oxford vr apt

Oxford Apartment with B&B amenities
A loft apartment rental adjacent to Sandaway Lodge.  Apartment has a king bedroom, sitting area, kitchen and full bath. Lite breakfast and morning paper are delivered each morning. Waterfront lawn and private beach. More info


More Oxford MD Vacation Rentals



Solomons Island MD


Cove Point Lighthouse Keeper’s Cottage
Here’s a unique vacation rental property! The Cove Point Lighthouse Keeper’s Cottage is listed on the National Register of Historic Places and is managed by the Calvert Marine Museum. The cottage sits on a seven acre point of land adjacent to the active Cove Point Light. The cottage is a duplex with a total of six bedrooms and 4.5 baths. Renovated for modern comfort with custom kitchens, central heat and a/c, screened porch, and washers and dryers. More info.


Waterfront Home Near Solomons
A waterfront home on the Potomac River with private dock and sandy beach. Three bedrooms and 2 baths. Large deck to enjoy the views. This home is well-equipped, with a gourmet kitchen, washer and dryer, BBQ, and a 2 person kayak. More info.

More Solomons Island Vacation Rentals

St Michaels MD

st michael vr in town

In Town Summer Vacation Cottage
Located in town and just steps away from everything.  Two bedrooms, two baths.  Well-equipped kitchen.  Outdoor grill
More info

More St Michaels Vacation Rentals

Tilghman Island MD

tilghman knap

“Knapp Shack” Brand New Waterfront Townhomn Overlooking the Bay
Views of Knapps Narrows and Chesapeake Bay.  Just steps away from the marina.  Three bedrooms, two and a half baths.
More info

tilghman cottage

Tilghman Island Cottage
Three bedrooms, two baths.  Located across from the marina.  Eat-in kitchen, four-season porch, and living room.
More info

More Tilghman Island Vacation Rentals

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