Eastern Shore Maryland Apartment Rentals & Vacation Rentals - 128 Rentals Available

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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 • Washer/Dryer
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 • Washer/Dryer
"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 / 11

St Michaels Home
3 BR / 3.5 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"The pictures do not do this house justice. It is a very big, open, airy home. It is advertised as 3 bedrooms, but really there are 4. The decks allow you to see the water no matter where you are on them. The 3 bedrooms each have sliding glass..."
- Kim Triplett Beck, York Haven, PA
(4) Excellent (4 reviews)
1 / 18

Ocean City Condo
2 BR / 2 BA / Sleeps 7 2 7 Min stay varies
Condo / 2 Bedrooms / Sleeps 7
2 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
"The place was very neat and clean. Beds were very comfy. plenty of space for my granddaughter to run around and veryclose to the beach. Short drive to the boardwalk. Able to use the hot tub and lap pool and the sauna and exercise room"
- BRIDGET BURGE, Middletown Md
(1) Excellent (1 review)
1 / 13

Ocean City Apartment
3 BR / 2 BA / Sleeps 10 3 10 No min stay
Apartment / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
Microwave • TV (Antenna) • Air Conditioning
"My stay at Ann's place was a WONDERFUL experience! ! It was a very accommodating place and the short walk to the beach was very convenient. I enjoyed every second of my stay. I would definitely book with them again."
- Melissa Garcia, Gaithersburg, MD
(2) Excellent (2 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 / 34

Centreville Home
4 BR / 2 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"We definitely enjoyed this house. So many interesting conversation pieces, and more books than you could possibly read on a vacation......all subjects. We especially enjoyed reading the book Alan had written himself....so much information about the..."
- Dee Keller, Pennsburg, Pennsylvania
(23) Excellent (23 reviews)
1 / 25

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 / 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 / 10

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
Dishwasher • Microwave • Air Conditioning
"This unit was our 1st private rental ever and we are very happy with our stay. The location is great with a park located directly across the street and a free fishing pier right next to it. Our children were happy to go play ball in the field and even..."
- JESSICA DIETRICH, Baltimore, Maryland, USA
(1) Excellent (1 review)
1 / 34

Ocean City Home
4 BR / 2.5 BA / Sleeps 10 4 10 Min stay varies
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"The house was absolutely beautiful and a perfect location for our family. The view of the bay was glorious. We enjoyed kayaking and relaxing on the dock. Dawn was very accommodating and handled our reservation with ease. This is a perfect location..."
- Chioma Fitzgerald, Clayton, NJ
(4) Excellent (4 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 • Washer/Dryer
"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 / 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

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 / 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 / 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 • Washer/Dryer
"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 / 11

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
"Thank you for letting us experience the place we love to go during our summer vacation. It felt just like home, everything was convenient, comfortable, and just what we needed! The view was beautiful and being able to watch my family enjoy the pool ..."
- Nikasha Miller -Reid, Morton, Pa.
(5) Excellent (5 reviews)
1 / 12

Ocean City Condo
Studio / 1 BA / Sleeps 4 0 4 Min stay varies
Condo / Studio / Sleeps 4
Studio 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"This place was in a great location close to everything never moved the car could walk to beach excellent people there were wonderful and and helpful they are all like family the owners pool is clean and so is area outside would recommend this place very..."
- theresa sellazzo, New York
(21) Excellent (21 reviews)
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)
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 / 12

Kent Island Home
4 BR / 3 BA / Sleeps 12 4 12 2 night min stay
Home / 4 Bedrooms / Sleeps 12
4 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"I rented this property for my sisters and their families during my wedding and it was fantastic. The owners were very easy to work with and the home was every it was advertised to be. My entire family was overwhelmed by the the home and it's beautiful..."
- Grant Weston, Austin, Texas
(4) Excellent (4 reviews)
1 / 21

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)
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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.