Holiday Homes in Eastern Maryland

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Eastern Maryland and around

Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
Cozy living space with a kitchen featuring a central stove, cabinetry, and a ceiling fan.

Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

9.6 out of 10, Exceptional, (109)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Relax on the covered balcony with a comfortable sofa and table, taking in the views of the surrounding cityscape.

⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

9.2 out of 10, Wonderful, (7)
"The location was amazing! Just steps from the beach! The condo was a perfect size for our family which was 5 adults and 2 young kids. It had everything we needed."
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Relax in a serene backyard oasis with Adirondack chairs, a table, and a chair, surrounded by a fence.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Wave Watcher's Condo - Steps to the beach!
Relax in a spacious living area with a sofa and dining table, featuring a washer and dryer.

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (7)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!
Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point
Stairs lead to a welcoming front door with a small porch area.

Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point

2.0 star property
10.0 out of 10, Exceptional, (16)
"Great place to stay great friendly people in neighorhood. Very clean and everything u need is right there in the house. Would definitely go back."
Coastal Cottage - 2BR Home with 2 Pools, pond, & 1000ft pier in Assateague Point
Sunset Island is Loved for it's Amazing Amenities
Relax by the pool surrounded by lounge chairs and umbrellas, with a gazebo and ocean views.

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
Bayfront cottage offers amazing views of the water and Assateague Island
Enjoy a serene view of the open field and water from this patio, featuring a comfortable seating area with a table and umbrella.

Bayfront cottage offers amazing views of the water and Assateague Island

9.6 out of 10, Exceptional, (40)
"Wonderful stay! Very clean and relaxing!"
Bayfront cottage offers amazing views of the water and Assateague Island
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Fridge, microwave, oven, stovetop

Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes

8.8 out of 10, Excellent, (3)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We were two families with children is different age groups. Everyone of us were comfortable in the property. Had a pleasant stay when not in the beach. All amenities were intact and suffice for a comfortable stay. OC beach is 30 minutes away and...
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️
Relax by the serene waterfront pool, surrounded by lounge chairs and umbrellas, with a picturesque view of the pier.

⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

9.4 out of 10, Exceptional, (12)
"My family loves Sunset Island. We thoroughly enjoyed staying at this condo. "
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Outdoor dining

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

The price is €2,363
includes taxes & fees
24 Aug - 25 Aug
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Water front, open bay views from both decks!!
Enjoy a serene view of the lake from the comfort of this room, featuring a large window and a spacious deck with a bench.

Water front, open bay views from both decks!!

10.0 out of 10, Exceptional, (69)
"Great place to stay!"
Water front, open bay views from both decks!!
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Step into this inviting home with a covered porch and glass door entrance, perfect for relaxing in a seating area with a sofa and coffee table.

Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

9.8 out of 10, Exceptional, (84)
"Alway enjoy staying at this property. "
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Charming dog-friendly townhouse with pool - near beach
Stylish residential building with attached balconies and a shaded walkway.

Charming dog-friendly townhouse with pool - near beach

8.0 out of 10, Very good, (109)
"Fine stay nice house. Easy to use codes. Beds comfortable. "
Charming dog-friendly townhouse with pool - near beach
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and sink.

Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool

9.8 out of 10, Exceptional, (44)
"This is a nice property located a short drive or "
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Lord Guy Retreat in Ocean Pines 3bd
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and white cabinetry.

Lord Guy Retreat in Ocean Pines 3bd

2.0 star property
Lord Guy Retreat in Ocean Pines 3bd
Very Spacious 3 level Bay Front vacation house
Enjoy the serene marina views from this balcony.

Very Spacious 3 level Bay Front vacation house

9.8 out of 10, Exceptional, (41)
"The property is in a great centrally located area. The house is amazing and as advertised with the gameroom being the main attraction. We'll definitely be returning."
Very Spacious 3 level Bay Front vacation house
1 BR 1.5 Canal Front Unit with Pool!
Step up to a tranquil retreat with access to the building via wooden steps and a railing.

1 BR 1.5 Canal Front Unit with Pool!

9.4 out of 10, Exceptional, (32)
"Excellent location very quiet area and close to everything,neighbors are very friendly.unit is perfect for a couple."
1 BR 1.5 Canal Front Unit with Pool!
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (129)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Eastern Maryland Hotel Reviews

Quality Inn Ocean City Beachfront

Quality Inn Ocean City Beachfront

10/10 Excellent
"I think that average good. "
Mohammad 1-night trip
Posted 12 hours ago
Quality Inn Ocean City Beachfront