Holiday Homes in Eastern Shore

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Featured Holiday Homes in Eastern Shore and around

Our top choices for Eastern Shore holiday homes

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €243
includes taxes & fees
3 Sept - 4 Sept
Relax on Kent Island in 3 Bedroom Home w/Waterview

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is €166
includes taxes & fees
1 Sept - 2 Sept
Cottage near the Bay

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is €163
includes taxes & fees
3 Sept - 4 Sept
Summer Rustic Camping with AC and King Bed

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
The price is €231
includes taxes & fees
1 Sept - 2 Sept
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Beautiful Bayside Landing!

8.6 out of 10, Excellent, (7)
"Great property to stay at! 10 minutes from the beach, but also in a quiet, clean, and safe neighborhood. Easy check in progress, clean property, and would definitely stay again!"
Beautiful Bayside Landing!

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (18)
"Loft was spotless, and had everything we needed. "
The price is €232
includes taxes & fees
2 Sept - 3 Sept
Cozy Barn Loft: Country Views & Central to Beaches

Salisbury Cottage

10.0 out of 10, Exceptional, (28)
"This property was very convenient to everything we needed. It was clean and well equipped and the hosts could not have been nicer or more attentive. We would definitely stay there again. Thank you for a wonderful stay."
Salisbury Cottage

Birdnest Beach Bungalow *Dog Friendly*

10.0 out of 10, Exceptional, (12)
"Nice visit "
Birdnest Beach Bungalow *Dog Friendly*

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (44)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is €389
includes taxes & fees
8 Sept - 9 Sept
Beautiful Waterfront Retreat in Cambridge!

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 €324
includes taxes & fees
3 Sept - 4 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is €267
includes taxes & fees
1 Sept - 2 Sept
BAYSIDE BUNGALOW

Cozy Makai Condo year-round pool access

8.0 out of 10, Very good, (1)
"In terms of the pros the location relative to the convention center was great and the condo overall was nice. The customer service team was also very responsive when the keypad no longer worked due to the battery dying. In terms of the cons we were unable to check in until around 4:20 as the cleaning staff was still there when we arrived at 4. The bathroom shower was a little dated and dirty looking compared to the pictures. "
Cozy Makai Condo year-round pool access

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 €327
includes taxes & fees
21 Sept - 22 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Salisbury Hideaway

10.0 out of 10, Exceptional, (19)
"We came to Salisbury to take a tour and this was the perfect place to stay. I was just about to book a hotel room when I found the Salisbury Hideaway. We appreciated how clean and fresh everything was. The kitchen and bathroom were well appointed and the beds were so comfortable. It was nice to have our own space. We woud definitely stay here again and recommend to friend's who have kids at SU. "
Salisbury Hideaway

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

10.0 out of 10, Exceptional, (3)
"Place was amazing. Super clean and host let us snacks and flowers, nice touch. Just wish zi would have asked if the pool access was inckuded. That is the only thing that could have made it any better. 10/10 recommend "
The price is €606
includes taxes & fees
1 Sept - 2 Sept
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is €304
includes taxes & fees
1 Sept - 2 Sept
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Harborview Retreat Mansion

10.0 out of 10, Exceptional, (1)
"Beautiful, clean and quiet community. We enjoyed our stay and would love to come back and stay again. "
The price is €670
includes taxes & fees
5 Sept - 6 Sept
Harborview Retreat Mansion

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is €321
includes taxes & fees
30 Sept - 1 Oct
Bayside Cottage steps from Rock Hall Harbor

Tangier Escape, great place get away from it all on Deal Island, MD.

The price is €181
includes taxes & fees
7 Sept - 8 Sept
Tangier Escape, great place get away from it all on Deal Island, MD.

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

9.8 out of 10, Exceptional, (116)
"Clean home, close to beach. Loved walking with coffee in hand to watch the sun rise! I would definitely stay again! "
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
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 Holiday Homes information

Number of reviews
Accommodation
468 Holiday Homes
Lowest Price
€166
Highest Price
€327