Eastern Shore Maryland Apartment Rentals & Vacation Rentals - 138 Rentals Available

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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 / 13

Ocean Pines 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
"Spent a few days at this rental with my family. It was very lovely. Would definitely stay again. Recommend it to anyone looking for a quiet southern stay."
- Patricia Carroll, Connecticut
(1) Excellent (1 review)
1 / 8

Ocean City Condo
1 BR / 1 BA / Sleeps 6 1 6 Min stay varies
Condo / 1 Bedroom / Sleeps 6
1 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Air Conditioning
"The condo was everything and more! It was beautiful, clean, plenty of room and so convenient! We had the best view every day overlooking the beach. It was on the first floor so we did not have to wait for the elevator long, the shed was great too ..."
- Nolita Mishler, Dundalk, MD
(17) Excellent (17 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 / 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 / 23

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
"Darlene was fantastic to deal with, her condo was spotless.The veiw was incredible from the indoor balcony to the master bedroom wall to wall view.The beach was not crowded and the heated pool felt great . This is the place to stay in OC."
- Chris Lewis, Baltimore
(5) Excellent (5 reviews)
1 / 10

Ocean City Condo
3 BR / 2 BA / Sleeps 10 3 10 Min stay varies
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
Dishwasher • Microwave • Air Conditioning
"Upon entering the condo we were impressed with how bright and clean it was. The bedrooms and baths were clean and the fact that we had three of each was a plus. Kitchen fully equipped and large and spacious. A definite rent again."
- Mariann Cangiano, Florida
(2) Excellent (2 reviews)
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 / 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 / 16

Ocean City Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"This was the most beautiful, clean condo. It is completely updated and spacious. The views from the balcony were so relaxing and peaceful in the evening. The building & grounds were clean & well maintained. We will definitely be coming back!"
- Jennifer Zuzo, Pittsburgh, pa
(9) Excellent (9 reviews)
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 / 35

Kent Island Home
4 BR / 3.5 BA / Sleeps 10 4 10 2 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"We stayed at the condo on Kent Island in late June 2016. The view is spectacular, the condo is spacious and the simple stylish decor is comfortable with abundant seating and space. Ten adults in our party stayed in the condo for 3 nights. Eight adults..."
- Laura Schwarz, Hanover, PA
(13) Excellent (13 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 / 17

Ocean City Condo
3 BR / 3 BA / Sleeps 9 3 9 3 night min stay
Condo / 3 Bedrooms / Sleeps 9
3 bedrooms 3 bathrooms Sleeps 9
Dishwasher • Microwave • Air Conditioning
"I stayed at this place with 9 of my friends and we had an amazing time. The house is spacious, clean and so close to everything. It has a huge porch (and another one off of the master bedroom) and it is less than a 10 minute walk to the beach. It has..."
- Laura Dowd, Bethesda, MD
(2) Excellent (2 reviews)
1 / 6

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
Dishwasher • Microwave • Air Conditioning
"Cute condo on the beach! Clean unit with a gorgeous ocean view. Our family had a great time and would definitely come back"
- Casey Beckmann Schmidt, Columbia, SC
(1) Excellent (1 review)
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 / 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 / 11

Ocean City Townhouse
3 BR / 2 BA / Sleeps 10 3 10 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
Dishwasher • Microwave • Air Conditioning
"What a lovely community! Don't have a negative comment to write! We truly enjoyed our stay with beautiful scenery and an awesome/huge property! Definitely will return next summer!"
- Matt Johnson, Nutley, NJ
(15) Excellent (15 reviews)
1 / 21

Ocean City Condo
4 BR / 3 BA / Sleeps 12 4 12 Min stay varies
Condo / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"Everything was exactly as noted in Owner's description. No issues at all with property. We had an awesome time, property is in a great central location on the strip."
- Austin Seid, Monroe, NY
(4) Excellent (4 reviews)
1 / 17

Ocean City Condo
2 BR / 2 BA / Sleeps 10 2 10 Min stay varies
Condo / 2 Bedrooms / Sleeps 10
2 bedrooms 2 bathrooms Sleeps 10
Dishwasher • Microwave • Air Conditioning
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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.