Holiday Homes in Eastern Shore

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Eastern Shore and around

Sunset Island is Loved for it's Amazing Amenities
Exterior

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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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
Beach

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
Marina

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 €446
includes taxes & fees
1 Sept - 2 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Wave Watcher's Condo - Steps to the beach!
Interior

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

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
Outdoor dining

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
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
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Outdoor pool

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.2 out of 10, Wonderful, (25)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor pool

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
Marina

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⭐️
Indoor pool, outdoor pool

⭐️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!
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

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 €274
includes taxes & fees
11 Aug - 12 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!
Exterior detail

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!
Exterior detail

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
Terrace/patio

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
Property grounds

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
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

Fenwick Inn

Fenwick Inn

10/10 Excellent
"unfortunately we were placed beside a room that had yippy dogs that barked all day and most of the night. We actually talked to front desk while their to report that the people were gone all day and never took there poor dog out! "
Tegan 5-night trip
Posted 16 hours ago
Fenwick Inn