3 BR / 3 BA / Sleeps 10 3 10 Min stay variesCondo / 3 Bedrooms / Sleeps 10
2 BR / 2 BA / Sleeps 6 2 6 7 night min Condo / 2 Bedrooms / Sleeps 6
1 BR / 1 BA / Sleeps 4 1 4 Min stay variesCondo / 1 Bedroom / Sleeps 4
3 BR / 2 BA / Sleeps 10 3 10 3 night min Condo / 3 Bedrooms / Sleeps 10
Studio / 1 BA / Sleeps 3 0 3 Min stay variesCondo / Studio / Sleeps 3
4 BR / 4.5 BA / Sleeps 14 4 14 Min stay variesTownhouse / 4 Bedrooms / Sleeps 14
2 BR / 1 BA / Sleeps 6 2 6 Min stay variesCottage / 2 Bedrooms / Sleeps 6
5 BR / 3.5 BA / Sleeps 18 5 18 Min stay variesHome / 5 Bedrooms / Sleeps 18
3 BR / 2 BA / Sleeps 9 3 9 2 night min Cottage / 3 Bedrooms / Sleeps 9
4 BR / 3.5 BA / Sleeps 8 4 8 No min stayTownhouse / 4 Bedrooms / Sleeps 8
4 BR / 3.5 BA / Sleeps 14 4 14 Min stay variesTownhouse / 4 Bedrooms / Sleeps 14
3 BR / 2 BA / Sleeps 6 3 6 Min stay variesHome / 3 Bedrooms / Sleeps 6
3 BR / 3 BA / Sleeps 6 3 6 7 night min Condo / 3 Bedrooms / Sleeps 6
2 BR / 1 BA / Sleeps 8 2 8 Min stay variesCondo / 2 Bedrooms / Sleeps 8
3 BR / 2 BA / Sleeps 8 3 8 Min stay variesCondo / 3 Bedrooms / Sleeps 8
3 BR / 2 BA / Sleeps 8 3 8 7 night min Condo / 3 Bedrooms / Sleeps 8
3 BR / 3 BA / Sleeps 9 3 9 Min stay variesCondo / 3 Bedrooms / Sleeps 9
3 BR / 2 BA / Sleeps 8 3 8 Min stay variesHome / 3 Bedrooms / Sleeps 8
7 BR / 6.5 BA / Sleeps 28 7 28 Min stay variesHome / 7 Bedrooms / Sleeps 28
1 BR / 1.5 BA / Sleeps 6 1 6 7 night min Condo / 1 Bedroom / Sleeps 6
2 BR / 1.5 BA / Sleeps 8 2 8 3 night min Condo / 2 Bedrooms / Sleeps 8
2 BR / 2 BA / Sleeps 8 2 8 Min stay variesCondo / 2 Bedrooms / Sleeps 8
About Eastern Shore
A beautiful coastal respite, Maryland’s Eastern Shore is the ideal place to escape from the hubbub of Washington, D.C. Choose from dozens of waterfront Eastern Shore vacation rentals, and plan your perfect getaway on the beach.
A true summer hotspot, Maryland’s Eastern Shore heats, with temperatures topping out around 90 degrees in the summer months of July and August. Winters tend to be moderate, with temperatures in the 40s. Those who want to enjoy fun in the sun should visit in the summer, while those looking for a quiet yet scenic respite should visit in the shoulder seasons of spring and fall.
The perfect location for an Atlantic road trip, Maryland’s eastern shore is best reached by car. Many visitors fly to one of the nearby Baltimore or Washington, D.C. airports and drive across the Chesapeake Bay Bridge to get to the area. Use your Eastern Shore vacation rental as a base for exploring, and travel from north to south on Highway 50, the main artery through the area.
Things to Do
If you’re seeking a tranquil spot on the shore, Cambridge and Easton offer small town charm with plenty of culture and nature to explore. During the day, make a trip to Blackwater National Wildlife Refuge, just south of Cambridge. Hike the Marsh Edge Trail or the Tubman Road Trail to see brackish marshes and bald eagles, or canoe one of the Water Trails for a new perspective of the Eastern Shore.
If you’re a nature lover, don’t miss Easton’s Pickering Creek Audubon Center, a 400-acre working farm that features four miles of hiking trails, bird watching areas, canoeing, and kid-friendly activities. In the evening, catch a performance at Easton’s Avalon Theatre, a historic performance space that hosts a range of traditional and contemporary singers and musicians.
Learn more about the Eastern Shore’s seafaring history in St. Michaels, home of the Chesapeake Bay Maritime Museum. Here visitors can see a working boatyard, try their hand at catching crabs at the wharf, immerse themselves in the area’s oystering industry, and learn about the St. Michaels steamboat building history.
For some quality time on the sand, head east to Ocean City. This fun-filled beach town has everything from long stretches of sand to a family-friendly boardwalk and seasonal events. Swim in the Atlantic waves, shop for souvenirs along the Ocean City Boardwalk, and catch a summer concert.
Thanks to its coastal location, Maryland’s Eastern Shore is a great place to find deliciously fresh seafood. For some of the freshest crab, try Hooked in Ocean City, which serves up everything from crab bisque to gourmet crab cakes. In St. Michaels, look no further than Waterman’s Crab House, which features crab pots and crab feasts with harbor views and live music. Other tasty and traditional regional fare includes fried clams, oyster fritters and Chicken Chesapeake. For dessert, treat the family to a slice of Smith Island Cake, a seven-layer cake that is also the official cake of Maryland.
Although the warmer months may draw the largest crowds to the region, tourists willing to brave the colder months will still find plenty of fun, local festivals and events to enjoy, including:
- WineFest at St. Michaels (April): A weekend festival that features local wine tastings, regional dishes from area chefs, and a variety of talented artists.
- National Hard Crab Derby (September): The crab-themed event features crab races, crab cooking and picking contests, carnival rides, beauty pageants, live entertainment, a parade and much more. The festival runs for an entire weekend and is a unique way to celebrate the region.
- Tilghman Day (October): As an annual festival celebrating Maryland’s seafood industry, this event includes oyster shucking and crab picking contests, as well as live music, vendors, and an auction.
- The Waterfowl Festival (November): Perfect for families that enjoy wildlife and the outdoors, this festival draws approximately 15,000 people annually and offers a variety of vendors and exhibitionists.
Whether you’re seeking a tranquil escape from the city or a fun beach getaway, the Chesapeake Bay has what you’re looking for. Book your Eastern shore condos before the season heats up, and enjoy beautiful views, fascinating history, and legendary food.