A marina with numerous boats docked at wooden piers under a clear sky.

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Our top choices for Eastern Shore vacation homes

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is ¥13,062
¥30,085 total
includes taxes & fees
Jul 9 - Jul 10
Cottage near the Bay

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (57 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥32,252
¥48,888 total
includes taxes & fees
Jul 8 - Jul 9
BAYSIDE BUNGALOW

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

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (105 reviews)
"This property and its owner were everything we look for in a vacation rental. Listing is as an old farm house does not do it justice. The owner has carefully curated it it with an electric collection of furniture ,pottery and various hand crafted items. She has put her heart and soul into this house and you can feel.it ad soon as you step inside. We will definitely be back.😍😍😍😍😍 The McCartney's and the Horneffs.......Thanks again for everything Laurie."
United States
Melinda
The price is ¥24,189
¥51,655 total
includes taxes & fees
Jul 6 - Jul 7
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.8 out of 10, Exceptional, (7 reviews)
"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."
United States
Rees L.
The price is ¥15,957
¥29,400 total
includes taxes & fees
Jul 8 - Jul 9
Summer Rustic Camping with AC and King Bed

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is ¥16,698
¥47,423 total
includes taxes & fees
Jul 6 - Jul 7
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is ¥43,562
¥70,938 total
includes taxes & fees
Jul 8 - Jul 9
Wren Retweet- Country Estate in Center of C’Town

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (23 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is ¥42,755
¥80,208 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (1 review)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is ¥26,366
¥29,956 total
includes taxes & fees
Jul 5 - Jul 6
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Amazing Bayfront views and Sunsets! Across the street from the beach!

Amazing Bayfront views and Sunsets! Across the street from the beach!
North Ocean City
10.0 out of 10, Exceptional, (50 reviews)
"We had a great stay, definitely recommend! "
United States
Bradley H.
The price is ¥50,822
¥95,049 total
includes taxes & fees
Jul 6 - Jul 7
Amazing Bayfront views and Sunsets! Across the street from the beach!

A Wave From it All | Screened Porch Outdoor Dining

A Wave From it All | Screened Porch Outdoor Dining
Ocean Pines
The price is ¥55,662
¥114,328 total
includes taxes & fees
Jul 9 - Jul 10
A Wave From it All | Screened Porch Outdoor Dining

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is ¥21,983
¥54,330 total
includes taxes & fees
Jul 9 - Jul 10
Charming Coastal/Country Home w/3 Acres & Sauna!

Come Hang at the Treehouse!

Come Hang at the Treehouse!
Midtown Ocean City
10.0 out of 10, Exceptional, (35 reviews)
"Gorgeous place with wonderful views !! "
United States
Susan H.
The price is ¥41,239
¥71,487 total
includes taxes & fees
Jul 9 - Jul 10
Come Hang at the Treehouse!

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is ¥36,284
¥58,023 total
includes taxes & fees
Jul 9 - Jul 10
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is ¥43,540
¥52,819 total
includes taxes & fees
Jul 19 - Jul 20
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Waterfront Haven - 4mi to Ocean City, MD Boardwalk - 4bdr/3.5ba; Sleeps 9

Waterfront Haven - 4mi to Ocean City, MD Boardwalk - 4bdr/3.5ba; Sleeps 9
Bayside
9.0 out of 10, Wonderful, (40 reviews)
"Our family enjoyed staying at this house. It is close to the boardwalk with out being right downtown. Thank you for sharing your home with us. "
United States
Maribeth L.
The price is ¥42,836
¥111,583 total
includes taxes & fees
Jul 6 - Jul 7
Waterfront Haven - 4mi to Ocean City, MD Boardwalk - 4bdr/3.5ba; Sleeps 9

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (20 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is ¥21,625
¥43,005 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Barn Loft: Country Views & Central to Beaches

OC/Fenwick Island Townhouse with Pool!

OC/Fenwick Island Townhouse with Pool!
North Ocean City
9.6 out of 10, Exceptional, (11 reviews)
"It was very clean and nice! Owner was very helpful with the entire trip. It was perfect location and lots of comfy beds."
United States
Emma D.
The price is ¥84,662
¥206,596 total
includes taxes & fees
Jul 12 - Jul 13
OC/Fenwick Island Townhouse with Pool!

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (39 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is ¥27,266
¥62,251 total
includes taxes & fees
Jul 5 - Jul 6
Salisbury Cottage

CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...
Ocean Pines
10.0 out of 10, Exceptional, (65 reviews)
"We had a great time. The house was nice, clean and was in a great location. We had a wonderful time! "
United States
Kim c.
The price is ¥72,603
¥144,561 total
includes taxes & fees
Jul 13 - Jul 14
CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (13 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is ¥57,821
¥109,005 total
includes taxes & fees
Jul 5 - Jul 6
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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

Eastern Shore Vacation Homes information

Number of reviews
582
Accommodation
513 Vacation Homes
Lowest Price
¥29,400
Highest Price
¥206,596

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