Holiday Homes in Eastern Maryland

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Featured Holiday Homes in Eastern Maryland

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⭐️

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."
The price is NZ$1,106
includes taxes & fees
1 Sept - 2 Sept
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

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!

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!

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

2.0 star property
10.0 out of 10, Exceptional, (17)
"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

Sunset Island is Loved for it's Amazing Amenities

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

8.8 out of 10, Excellent, (3)
"property was very clean, lot of space everything was equipped in kitchen for cooking. plus kids toys. We had a great time staying that the property."
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes

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⭐️

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+

The price is NZ$4,514
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!!

10.0 out of 10, Exceptional, (70)
"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!

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

8.0 out of 10, Very good, (110)
"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

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

2.0 star property
Lord Guy Retreat in Ocean Pines 3bd

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!

9.4 out of 10, Exceptional, (33)
"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

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