Eastern Shore Maryland Apartment Rentals & Vacation Rentals - 141 Rentals Available

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1 / 23

Ocean City Condo
3 BR / 3 BA / Sleeps 10 3 10 Min stay varies
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"This rental is great. Comfortably sleeps 10. It was like home away from home, very comfortable, nice beds in each room, nice TV's in each room and very spacious overall. Bathrooms are also nice. Nicely finished with a home atmosphere that our family..."
- Adrienne Anderson-Ferrell, Hockessin, DE
(2) Excellent (2 reviews)
1 / 35

Ocean City Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This is such a great place with beautiful views from the bottom and top floor decks. There is everything you could possibly need and the owner was great. We had our dogs with us and they had a great time too. I would definitely recommend this place..."
- Dorothy Jane Grisolia, River Vale, NJ
(7) Excellent (7 reviews)
1 / 22

Ocean City Condo
3 BR / 2 BA / Sleeps 10 3 10 3 night min stay
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"This is a great three bedroom condo! We had everything we needed and more. Access to so many TVs was awesome since we each had different tastes relative to TV programs. The location was perfect with an outstanding view of the ocean. Only one small..."
- Carole Robertson, Middletown, Delaware USa
(6) Excellent (6 reviews)
1 / 24

Ocean City Condo
Studio / 1 BA / Sleeps 3 0 3 Min stay varies
Condo / Studio / Sleeps 3
Studio 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
"My husband and our six year old daughter went for a quick getaway this past week- end, and we stayed at here. It by far exceeded our expectations. The beachfront view is breath taking, the place was very quaint and just perfect for our small family...."
- Nafeesah S. Carter, Baltimore, MD
(18) Excellent (18 reviews)
1 / 28

Cambridge Home
5 BR / 3.5 BA / Sleeps 18 5 18 Min stay varies
Home / 5 Bedrooms / Sleeps 18
5 bedrooms 3.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
"Our extended family of 18 people had a wonderful vacation experience at Spocott. There was something for all ages to do. Our boys (and son- in laws, too) loved the crabbing and the last night of our vacation we had a " crab fest". The owners of Spocott..."
- David Overdorf, Nazareth, PA
(2) Excellent (2 reviews)
1 / 22

Cambridge Cottage
3 BR / 2 BA / Sleeps 9 3 9 2 night min stay
Cottage / 3 Bedrooms / Sleeps 9
3 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
"Absolutely beautiful placeA lot to do and we didn't even have to leave the property. Fishing, crabbing, canoeing, the pool.everybody was very comfortable to do whatever they felt, adults and the children. The house was a charm"
- Laverne Adams, West Caln, Pa
(6) Excellent (6 reviews)
1 / 24

Ocean City Townhouse
4 BR / 3.5 BA / Sleeps 8 4 8 No min stay
Townhouse / 4 Bedrooms / Sleeps 8
4 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Property is convenient to the beach. It is new, spacious and comfortable. Range cooktop is one of those infrared things - hard to cook on. Short on good pans and knives. There are pans and knives - probably ofthe quality one should expect in a ..."
- Dave Ridge, Illinois - where we have no water views. Why we go to the beach for units with water views.
(1) Excellent (1 review)
1 / 26

Ocean City Townhouse
4 BR / 3.5 BA / Sleeps 14 4 14 Min stay varies
Townhouse / 4 Bedrooms / Sleeps 14
4 bedrooms 3.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
"The townhouse was in a great location for both the beach and for other activities in Ocean City! The house had plenty of room for large groups and I would definitely recommend staying here to a friend, or stay here again myself! Lots of close parking..."
- Lauren Pettengill, Virginia
(26) Excellent (26 reviews)
1 / 22

Ocean Pines Home
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Great house, great location. Near grocery store, restaurants, Ocean Downs Casino, 15 minutes to beach, Ocean City Boardwalk. The Ocean Pines community is very nice. Plenty of room- we had 4 adults and 1 child. The house is clean and has comfortable..."
- Cathy Iadovito, Buffalo NY
(14) Excellent (14 reviews)
1 / 16

Ocean City Condo
3 BR / 3 BA / Sleeps 6 3 6 7 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"Location, location, Location. Lots of room and some new decor."
- Victor DAquino, Brooklyn NY
(1) Excellent (1 review)
1 / 16

Ocean City Condo
2 BR / 1 BA / Sleeps 8 2 8 Min stay varies
Condo / 2 Bedrooms / Sleeps 8
2 bedrooms 1 bathroom Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Beautiful condo with plenty of space for the whole family ! !"
- Kara Thompson Topper, Fairfield Pennsylvania
(1) Excellent (1 review)
1 / 29

Ocean City Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We had a wonderful time, like our own private vacation. Great place for a family to relax, and have fun."
- JoAnn Stoffregen, Baltimore maryland
(6) Very Good (6 reviews)
1 / 22

Ocean City Condo
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We had a wonderful experience ! The place was beautiful. Very clean! Very toddler friendly! The kids and adults both had a great time! And we really enjoyed our stay! Will definitely be back!"
- Kristi McAtee, Abingdon, MD
(18) Excellent (18 reviews)
1 / 16

Ocean City Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This is a georgous house that is comfortable and really makes the trip worth while. It's a short walk to the beach and has a great view right on the sound!"
- Mary Suzanne, Baltimore, MD
(16) Excellent (16 reviews)
1 / 35

Cambridge Home
7 BR / 6.5 BA / Sleeps 28 7 28 Min stay varies
Home / 7 Bedrooms / Sleeps 28
7 bedrooms 6.5 bathrooms Sleeps 28
High Speed Internet • Dishwasher • Microwave
"Perfectly lovely. After the sale of a home that was our Thanksgiving Tradition for 40 years we were looking for a new tradition. The home was well appointed, the kitchen perfectly supplied with extra space. The little cousins had a blast in their ..."
- Deirdre Lofft, MD
(9) Excellent (9 reviews)
1 / 12

Ocean City Condo
1 BR / 1.5 BA / Sleeps 6 1 6 7 night min stay
Condo / 1 Bedroom / Sleeps 6
1 bedrooms 1.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We had a great time staying at Scott's condo at the East Winds East in Oc.......The place was really nice & it felt like home....eveything was neat and clean and the view of the ocean was magnificent! ! ......They had 2 large flat screen TV's and internet..."
- Linda Heckner, In Belair Maryland
(10) Excellent (10 reviews)
1 / 12

Ocean City Condo
2 BR / 1.5 BA / Sleeps 8 2 8 3 night min stay
Condo / 2 Bedrooms / Sleeps 8
2 bedrooms 1.5 bathrooms Sleeps 8
Dishwasher • Microwave • Air Conditioning
"It was a short walk to the beach...a few blocks, but we didn't have to cross coastal highway, which was nice. The condo was very quaint and newly remodeled (no elevator). The location was great and very close to the park, restaurants etc."
- Maria Colamonaco Kelly, Bel Air, MD
(1) Excellent (1 review)
1 / 25

Ocean City Condo
2 BR / 2 BA / Sleeps 8 2 8 Min stay varies
Condo / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"Randy, Thanks a million for the use of your condo 2005 ocean city the condo was beautiful as were the views from both sides was not sure if the bayside balcony was just for your condo or one next to it also it became packed watching fireworks july 4th..."
- Levi Morgan, altoona pennsylvania
(51) Excellent (51 reviews)
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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.

Climate

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.

Transit

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.
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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.

Food

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.

Events

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.