Eastern Maryland Vacation Rentals

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Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Eastern Maryland Vacation Homes

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
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, (43)
"This is a nice property located a short drive or "
Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Enjoy meals in the kitchen with a stove, oven, and dining area.

Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community

10.0 out of 10, Exceptional, (7)
Beautiful 3 BR 2.5 BA New Home in West Ocean City's Bayside Community
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Overlooking a wide sandy beach, this property offers stunning views of the calm sea.

Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More

9.4 out of 10, Exceptional, (19)
"Well cared for"
Downtown Perch W/ Free WiFi, Private Balcony/Patio, Easy Beach Access & More
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $386
CA $697 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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, (6)
"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!
Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD
Relax on the deck with comfortable seating and dining areas overlooking the beach.

Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD

9.6 out of 10, Exceptional, (44)
"Highly recommend and will surly book again"
Beach Cove: Ocean Front 4Bed/2Bath - Ocean City MD
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, (165)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle
Fully equipped kitchen with a marble countertop and white tiled floor.

Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle

9.2 out of 10, Wonderful, (12)
"We love Bayside Resort. This house was perfect for our family’s needs. They included nice amenities like dog bowls and kids books. Love Bayside’s pool and the kayaks on Assawoman Bay."
Bayside escape with pools, golf, tennis, fishing, spas & saunas + beach shuttle
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
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
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⭐️

9.6 out of 10, Exceptional, (11)
"My family loves Sunset Island. We thoroughly enjoyed staying at this condo. "
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️
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, (107)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
Quiet Beachfront Retreat with Private Balcony
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and refrigerator.

Quiet Beachfront Retreat with Private Balcony

8.2 out of 10, Very good, (25)
"The unit is very close to the beach."
Quiet Beachfront Retreat with Private Balcony
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!
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, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Spacious and Modern Luxury Villas conveniently located on 104th St
Welcome to 10401, a hotel with a striking entrance and expansive windows.

Spacious and Modern Luxury Villas conveniently located on 104th St

8.8 out of 10, Excellent, (13)
"Great trip. The property was as promised. Zero complaints. Definitely will stay again next year"
Spacious and Modern Luxury Villas conveniently located on 104th St
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

Fenwick Inn

Fenwick Inn

10/10 Excellent
"The staff, pool area was awesome"
Devin 1-night trip
Posted 8 hours ago
Fenwick Inn