Eastern Shore Hotel Guide - Hotels with Pool in Eastern Shore, Maryland
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Our top choices for Eastern Shore hotels with a pool
9.0 out of 10, Wonderful, (3366)
"Yes, I great place y to o stay"
James
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (939)
"It was very comfortable and clean"
Maria
The price is €82
includes taxes & fees
1 Jan - 2 Jan 2026
9.2 out of 10, Wonderful, (1001)
"Amazingly friendly staff. Welcoming and heart warming, had to extend a night due to car issues, they were able to facilitate us with no issues, and being a part of hilton honors it's like going home."
Haitham
The price is €88
includes taxes & fees
23 Jan - 24 Jan 2026
9.0 out of 10, Wonderful, (1104)
"Love the fact that the hotel is footsteps away from the beach and the view is amazing!!"
Elliott
The price is €69
includes taxes & fees
6 Jan - 7 Jan 2026
DoubleTree by Hilton Ocean City Oceanfront
DoubleTree by Hilton Ocean City OceanfrontMidtown Ocean City
9.0 out of 10, Wonderful, (1000)
"Beautiful and spotless room. The oceanfront view was so nice to wake up to in the morning. The staff were all very friendly. The restaurant on site Marlin Moon was outstanding. "
Kristin
The price is €79
includes taxes & fees
6 Jan - 7 Jan 2026
9.0 out of 10, Wonderful, (1591)
"Room was excellent, very clean, not dated at all, location oceanfront was great - fantastic view of the sunrise. "
David
The price is €75
includes taxes & fees
6 Jan - 7 Jan 2026
9.2 out of 10, Wonderful, (1062)
"Great location, friendly staff."
Yun-Ping
9.2 out of 10, Wonderful, (1006)
"Room was clean and staff was great"
Jeanette
The price is €83
includes taxes & fees
6 Jan - 7 Jan 2026
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.
Top Eastern Shore Hotel Reviews
Grand Hotel Ocean City Oceanfront
10/10 Excellent
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