Holiday Homes in Eastern Shore

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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 Shore 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
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

8.0 out of 10, Very good, (2)
"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
Stay & Play at Our Beautiful Retreat
Surrounded by lush trees, this pool offers a serene escape.

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat
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⭐️
Pet-Friendly Home on Chester River w/ Dock!
Relax in a spacious, open-plan room with multiple seating areas and large windows offering a view of the outdoors.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Historic home on Smith Island w/ dock!
Enjoy serene views of the calm water from the dock, surrounded by a peaceful shoreline.

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Outdoor dining

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

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!!
Relax on Kent Island in 3 Bedroom Home w/Waterview
Overlooking the marina, the city skyline shines brightly.

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €296
includes taxes & fees
28 Aug - 29 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview
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
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 Shore 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 6 hours ago
Quality Inn Ocean City Beachfront