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3 Oct - 5 Oct
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Browse Select Upper Hooper Island Cottages

Walk to Beach: Charming Maryland Home w/ Yard!
House (2 Bedrooms) | Interior

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
House (5 Bedrooms) | Front of property

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Bayfront Gem w/ Amazing Water Views + Pond!
Front of property

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!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
Beachy Maryland A-frame: Steps to Chesapeake Bay!
House (3 Bedrooms) | Interior

Beachy Maryland A-frame: Steps to Chesapeake Bay!

3.0 star property
Beachy Maryland A-frame: Steps to Chesapeake Bay!
Beautiful Colonial Home on the Choptank River
House (4 Bedrooms) | Interior

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
Waterfront Cambridge Home: Pool & Dock!
House (4 Bedrooms) | Interior

Waterfront Cambridge Home: Pool & Dock!

3.0 star property
Waterfront Cambridge Home: Pool & Dock!
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
House (2 Bedrooms) | Interior

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

3.0 star property
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Walk to Beach: Elegant Escape in Lusby!
House (4 Bedrooms) | Interior

Walk to Beach: Elegant Escape in Lusby!

3.0 star property
Walk to Beach: Elegant Escape in Lusby!
Sunrise Views: Waterfront Lusby Home w/ Deck!
House (4 Bedrooms) | Front of property

Sunrise Views: Waterfront Lusby Home w/ Deck!

3.0 star property
Sunrise Views: Waterfront Lusby Home w/ Deck!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
House (Multiple Bedrooms) | Interior

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

3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Screened Patio, Deck & Grill: Saint Inigoes Home!
House (3 Bedrooms) | Interior

Screened Patio, Deck & Grill: Saint Inigoes Home!

3.0 star property
Screened Patio, Deck & Grill: Saint Inigoes Home!
Near Solomons Island Boardwalk: Home w/ Hot Tub!
House (3 Bedrooms) | Interior

Near Solomons Island Boardwalk: Home w/ Hot Tub!

3.0 star property
Near Solomons Island Boardwalk: Home w/ Hot Tub!
Waterfront House With Dock, Kayaks, & Sailboat!
House (4 Bedrooms) | Front of property

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views
House (Multiple Bedrooms) | Interior

Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views

3.0 star property
Bay Estate Luxe Waterfront Home w/ Private Pier, Main+guest House, Bay Views
Walk to Beach: Pet-friendly Gem in Scotland!
Cottage (1 Bedroom) | Interior

Walk to Beach: Pet-friendly Gem in Scotland!

3.0 star property
Walk to Beach: Pet-friendly Gem in Scotland!
Maryland Vacation Rental w/ Private Pool & Dock
House (4 Bedrooms) | Interior

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Scotland Beach Retreat w/ Private Beach
House (4 Bedrooms) | Interior

Waterfront Scotland Beach Retreat w/ Private Beach

3.0 star property
Waterfront Scotland Beach Retreat w/ Private Beach
Historic Hoopersville Getaway on Chesapeake Bay!
House (Multiple Bedrooms) | Interior

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!
Bay Cottage by Avantstay Waterfront, Pier, Pond
Exterior

Bay Cottage by Avantstay Waterfront, Pier, Pond

3.0 star property
Bay Cottage by Avantstay Waterfront, Pier, Pond
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Beautiful place"
Neil 1-night trip
Posted 5 days ago
Hyatt Regency Chesapeake Bay

Find out more about Upper Hooper Island

Find out more about Upper Hooper Island

Upper Hooper Island Cottages information

Number of reviews
1
Accommodation
36 Cottages
Lowest Price
Highest Price