Search Cottages in Upper Hooper Island

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 26 - Sep 28
In two months
Nov 7 - Nov 9
In three months
Dec 5 - Dec 7
In four months
Jan 2 - Jan 4

Cottages in Upper Hooper Island

Our top choices for Upper Hooper Island cottages

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!
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
Walk to Beach: Charming Maryland Home w/ Yard!
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!
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!
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!
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!
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
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!
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
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
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!
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Interior

Waterfront Lusby Retreat w/ Deep-water Dock & Slip

3.0 star property
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Hooper Island Hotel Reviews

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"Newly renovated rooms and bar area. Beds are comfortable "
Shannon 3-night trip
Posted 8 days ago
Solomons Inn Resort & Marina
Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Breakfast is good"
Vy 1-night trip
Posted 1 month ago
Comfort Inn & Suites

Find out more about Upper Hooper Island

Find out more about Upper Hooper Island

Upper Hooper Island Cottages information

Number of reviews
Accommodation
36 Cottages
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia