Search Cottages in Upper Hooper Island

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Upper Hooper Island

Bayfront Gem w/ Amazing Water Views + Pond!
Enjoy a serene ocean view from the covered deck, overlooking the water and adjacent grassy area.

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!
Relax on the deck with a clear view of the water, surrounded by a tranquil atmosphere.

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
Relax in a serene outdoor space with a clear view of the water and dock, surrounded by lush greenery and comfortable seating.

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!
Stunning single-story home with a charming front porch and beautifully manicured lawn.

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
Stylish two-story home with a garage, porch, and lawn.

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Beachy Maryland A-frame: Steps to Chesapeake Bay!
Interior

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!
Front of property

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
Interior

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront House With Dock, Kayaks, & Sailboat!
Stunning two-story house with a central entrance and covered porch, set amidst lush green lawns and a tree-lined pathway.

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Enjoy al fresco dining with a grill and lake views from this outdoor patio.

Screened Patio, Deck & Grill: Saint Inigoes Home!

3.0 star property
Screened Patio, Deck & Grill: Saint Inigoes Home!
Historic Hoopersville Getaway on Chesapeake Bay!
Stunning two-story home with a central entrance and porch, set amidst a lush green lawn.

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!
Bay Views & Fire Pit: Taylors Island Retreat
Relax in a serene outdoor space with wicker furniture and a glass-top table overlooking a tranquil body of water.

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!
Relax in the serene outdoor patio, surrounded by lush greenery and trees, with a shaded table and comfortable seating for four.

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!
Welcome to this charming single-story home with a cozy porch and beautifully manicured lawn.

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!
Interior

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!
Interior

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
Interior

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
Interior

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
Relax in this inviting outdoor seating area with a sofa, chair, and table.

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!
Relax on the deck with a view of the water and a pier, surrounded by comfortable seating and a shaded area.

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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