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Browse Select Upper Hooper Island Cottages

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace

Beachy Maryland A-frame: Steps to Chesapeake Bay!

3.0 star property
Beachy Maryland A-frame: Steps to Chesapeake Bay!

Sunrise Views: Waterfront Lusby Home w/ Deck!

3.0 star property
Sunrise Views: Waterfront Lusby Home w/ Deck!

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!

Screened Patio, Deck & Grill: Saint Inigoes Home!

3.0 star property
Screened Patio, Deck & Grill: Saint Inigoes Home!

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!

Bay Views & Fire Pit: Taylors Island Retreat

3.0 star property
Bay Views & Fire Pit: Taylors Island Retreat

1915 Historic Cambridge Property w/ Fire Pit!

3.0 star property
1915 Historic Cambridge Property w/ Fire Pit!

Modern Solomons Cottage Rental - Walk to Island!

3.0 star property
Modern Solomons Cottage Rental - Walk to Island!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Family-friendly Cambridge Home w/ Fire Pit!

3.0 star property
Family-friendly Cambridge Home w/ Fire Pit!

Waterfront Scotland Beach Retreat w/ Private Beach

3.0 star property
Waterfront Scotland Beach Retreat w/ Private Beach

Vacation Rental House Situated on Chesapeake Bay

3.0 star property
Vacation Rental House Situated on Chesapeake Bay

Waterfront Lusby Retreat w/ Deep-water Dock & Slip

3.0 star property
Waterfront Lusby Retreat w/ Deep-water Dock & Slip

Choptank River Beach Home w/ Pier in Cambridge!

3.0 star property
Choptank River Beach Home w/ Pier in 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 Upper Hooper Island Hotel Reviews