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Vacation Homes in Eastern Shore

Our top choices for Eastern Shore vacation homes

⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

8.8 out of 10, Excellent, (9)
"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 ¥43,211
¥97,344 total
includes taxes & fees
Sep 1 - Sep 2
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

1 BR 1.5 Canal Front Unit with Pool!

9.4 out of 10, Exceptional, (35)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was as expected. Had no issues. Liked the back deck on the water."
1 BR 1.5 Canal Front Unit with Pool!

Sunset Island is Loved for it's Amazing Amenities

10.0 out of 10, Exceptional, (2)
"Very nice house. Like the key code entry instead of keys.Some in our group made use of the gym, pool, and bay beaches. Felt safe to let pre-teens and teens walk on their own. Kitchen could use more mugs, silverware, cooking utensils, and potholders.Six passes for a house that accommodates 12 is odd, so we took turns to avoid the expense of more passes. Other parts of the island would be a closer walk for the ocean, but it was doable."
Sunset Island is Loved for it's Amazing Amenities

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is ¥11,943
¥27,820 total
includes taxes & fees
Sep 1 - Sep 2
Cottage near the Bay

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (40)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Waterfront Getaway-walk to beach and local favorites!

10.0 out of 10, Exceptional, (36)
"Our 1st time in Maryland and it was wonderful!!"
Waterfront Getaway-walk to beach and local favorites!

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

10.0 out of 10, Exceptional, (91)
"Enjoying Can’t wait to stay again"
The price is ¥22,160
¥46,735 total
includes taxes & fees
Aug 28 - Aug 29
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (9)
"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!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Quiet Beachfront Retreat with Private Balcony

8.4 out of 10, Very Good, (26)
"The unit is very close to the beach."
Quiet Beachfront Retreat with Private Balcony

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

9.6 out of 10, Exceptional, (111)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

Water front, open bay views from both decks!!

10.0 out of 10, Exceptional, (73)
"Great place to stay!"
Water front, open bay views from both decks!!

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach

Beach Cottage 1Bed/1Bath Fully Renovated on the Boardwalk

9.8 out of 10, Exceptional, (51)
"Great location, clean, walkable to everything, perfect place to watch the car show."
Beach Cottage 1Bed/1Bath Fully Renovated on the Boardwalk

< 1 Mi to Boardwalk: Ocean City Retreat on Canal

< 1 Mi to Boardwalk: Ocean City Retreat on Canal

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (12)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ¥25,804
¥58,143 total
includes taxes & fees
Aug 28 - Aug 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

DownByTheBay_107- Spacious Beach Home 4BR/3.5BA @Broad Marsh/Pool/Steps to Beach

9.4 out of 10, Exceptional, (36)
"The property was easy to find, exceptionally clean, and very enjoyable! Would definitely book again!"
DownByTheBay_107- Spacious Beach Home 4BR/3.5BA @Broad Marsh/Pool/Steps to Beach

Sailor's Sunrise Cottage - Chesapeake Bay

9.6 out of 10, Exceptional, (51)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

Charming Getaway with Boat Dock Minutes from Ocean City

9.4 out of 10, Exceptional, (19)
"Awesome location and house. Plenty of room, everything was very clean and comfortable. Hope to stay there again in the future. Property owner was very nice and helpful. "
Charming Getaway with Boat Dock Minutes from Ocean City
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

Find out more about Eastern Shore

Find out more about Eastern Shore

Eastern Shore Vacation Homes information

Number of reviews
828
Accommodation
464 Vacation Homes
Lowest Price
¥11,943
Highest Price
¥43,211

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