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Vacation Homes in Eastern Shore

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"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

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is SAR 304
SAR 708 total
includes taxes & fees
8 Sep - 9 Sep
Cottage near the Bay

Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

9.8 out of 10, Exceptional, (17)
"Would stay again "
The price is SAR 657
SAR 1,762 total
includes taxes & fees
24 Sep - 25 Sep
Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (47)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
BAYSIDE BUNGALOW

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

10.0 out of 10, Exceptional, (91)
"The property was great. Large kitchen, comfortable beds, and an amazing outdoor area. Laurie was friendly, responsive, and very accommodating. "
The price is SAR 750
SAR 1,404 total
includes taxes & fees
8 Oct - 9 Oct
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!

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

9.8 out of 10, Exceptional, (135)
"Great place nice location visited the beach every day. Great Hosts! "
The price is SAR 469
SAR 1,466 total
includes taxes & fees
5 Oct - 6 Oct
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (192)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

9.4 out of 10, Exceptional, (63)
"Our stay was very nice "
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

Charming Canal Water View Townhome with Outdoor Pool, WiFi & AC in Ocean City

10.0 out of 10, Exceptional, (8)
Charming Canal Water View Townhome with Outdoor Pool, WiFi & AC in Ocean City

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!

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"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

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown

⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

9.4 out of 10, Exceptional, (14)
"My family loves Sunset Island. We thoroughly enjoyed staying at this condo. "
⭐️Gorgeous Sunset Island Private Beach In/Outdoor Pools⭐️

Quiet Beachfront Retreat with Private Balcony

8.4 out of 10, Very Good, (27)
"The place is small but has a nice view. Definitely take bath towels. "
Quiet Beachfront Retreat with Private Balcony

Ocean Front 4 bedroom 3 bath

9.0 out of 10, Wonderful, (7)
"Positives: The unit is beautiful. Short walk to the beach, plenty of room for our family. Host was initally responsive, the first day. Negatives: We were suppose to be in at 3pm, cleaners didn’t finish until 3:30. My kids found a pack of cigarettes under the couch (we don’t smoke). The refrigerator took 36 hours to cool down, we had to put all of our groceries in coolers. Upon getting to the unit, the back screen door was broke and not fixable. Master bedroom door hinges were pulling out of the...
Ocean Front 4 bedroom 3 bath

Charming house & casita near the ocean with private pool, W/D & central AC

8.0 out of 10, Very Good, (38)
"We are OC locals and did a staycation for my husband’s 52nd birthday. The property was spacious. The two houses in one location was great foe privacy."
Charming house & casita near the ocean with private pool, W/D & central AC

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

The price is SAR 5,610
SAR 9,042 total
includes taxes & fees
28 Sep - 29 Sep
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

9.0 out of 10, Wonderful, (93)
"The house is big and beautiful and was very clean and comfortable. "
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

SOUTH BEACH 601 ULTRA LUXURIOUS BOARDWALK GYM IN/OUT POOL

8.8 out of 10, Excellent, (28)
"Property was beautiful, kitchen should be restocked, 2 of the beds need new mattresses, more lighting for reading in the living area, easier access to building, luggage carts for easier transport from car to room! We are very happy with the rental over all"
SOUTH BEACH 601 ULTRA LUXURIOUS BOARDWALK GYM IN/OUT POOL
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