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Compare 492 Vacation Homes in Eastern Shore with updated reviews, rates, and availability.

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (38)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is AED 735
AED 1,098 total
includes taxes & fees
1 Jun - 2 Jun
BAYSIDE BUNGALOW

Spacious and modern luxury construction for your beach vacation

9.2 out of 10, Wonderful, (18)
"it's a new property and very close to beach"
Spacious and modern luxury construction for your beach vacation

4-story bayfront townhouse with canal views, 2 decks, private dock, griddle, AC

9.2 out of 10, Wonderful, (5)
"Loved the layout. We went with a group of adults(no kids)and it was cool we had our own space but we were still close enough to each other."
4-story bayfront townhouse with canal views, 2 decks, private dock, griddle, AC

Stunning 2 story luxury villa on 104th Street

8.4 out of 10, Very Good, (16)
"We had a great stay. The house is well furnished, clean modern and well located."
Stunning 2 story luxury villa on 104th Street

Cottage near the Bay

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"
The price is AED 331
AED 724 total
includes taxes & fees
31 May - 1 Jun
Cottage near the Bay

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (260)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (18)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

2 North Ocean Block Townhome 4 bed/3.5 bath Sleeps 14, Ocean View Top Floor

8.4 out of 10, Very Good, (47)
"Very good property for the price. "
2 North Ocean Block Townhome 4 bed/3.5 bath Sleeps 14, Ocean View Top Floor

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

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

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay... Easy access to groceries, and plenty of parking."
Ocean City Bayside Retreat Unit A - Cozy Family Getaway Near Beach & Dining!

⭐️Gorgeous 2 Story Oceanfront Penthouse Heated Pool Sauna⭐️

9.4 out of 10, Exceptional, (15)
"Very nice place with a great view! Plenty of room for everyone. "
⭐️Gorgeous 2 Story Oceanfront Penthouse Heated Pool Sauna⭐️

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.4 out of 10, Exceptional, (34)
"We enjoyed our stay in this condo with everything. Conveniently located, we loved the ocean views near the boardwalk. Restaurants and shops located nearby were a plus. The kitchen was well equipped and the bathrooms were spacious, not cramped. We would definitely stay here again!"
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

Quiet coastal home with patio & pool, close to Assateague & Ocean City

8.6 out of 10, Excellent, (13)
"Nice place unfortunately it rained but overall the community was very clean and quiet "
Quiet coastal home with patio & pool, close to Assateague & Ocean City

An escape for all seasons

9.8 out of 10, Exceptional, (42)
"The location, house layout and "at home" feeling make this an amazing property for a family vacation. It's far enough off the beach to enjoy the peacefulness of the area but close enough to drive in for all the activities."
An escape for all seasons

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (35)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 328
AED 1,044 total
includes taxes & fees
2 Jun - 3 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

Driftwood - a Beautiful 3 Bedroom, 2.5 Bath Townhome in the Heart of OCMD!

10.0 out of 10, Exceptional, (3)
"Overall great spot."
Driftwood - a Beautiful 3 Bedroom, 2.5 Bath Townhome in the Heart of OCMD!

Cozy suite in oceanfront condo with indoor pool, balcony, gym, & central AC

8.0 out of 10, Very Good, (15)
"Spacious rooms, quaint furnishings. Great access to the beach. Indoor pool is very nice."
Cozy suite in oceanfront condo with indoor pool, balcony, gym, & central AC

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"The property was great, clean and spacious. The views were remarkable and amenities exactly what we needed while we are working a major event."
Chesapeake Bay House with Dock & Private Beach

Alexander Mini Mansion in the Heart of Downtown OC

6.0 out of 10, (1)
Alexander Mini Mansion in the Heart of Downtown OC

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (8)
"This stay was perfect. The location was charming and safe, and the home was clean and cozy. Jennifer was a very accommodating and responsive host."
The price is AED 826
AED 1,631 total
includes taxes & fees
9 Jun - 10 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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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