Search Upper Hooper Island Cottage Rentals

    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

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Upper Hooper Island

Walk to Beach: Charming Maryland Home w/ Yard!
Enjoy a serene beach experience with access to calm waters and a picturesque jetty.

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!
Bayfront Gem w/ Amazing Water Views + Pond!
Enjoy a serene view of the water from the comfort of this room, featuring a cozy reading nook with a vase of flowers and a book.

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Riverside House w/ Kayaks, Piano & Fireplace
Enjoy cooking in the well-equipped kitchen with a central island, sink, and ample counter space, complemented by a large window.

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
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
Enjoy cooking in this well-lit kitchen with a central island, stove, and granite countertop.

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
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!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Enjoy cooking and socializing in this kitchen with a central island and bar stools.

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

3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Near Solomons Island Boardwalk: Home w/ Hot Tub!
Front of property

Near Solomons Island Boardwalk: Home w/ Hot Tub!

3.0 star property
Near Solomons Island Boardwalk: Home w/ Hot Tub!
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
Walk to Beach: Pet-friendly Gem in Scotland!
Interior

Walk to Beach: Pet-friendly Gem in Scotland!

3.0 star property
Walk to Beach: Pet-friendly Gem in Scotland!
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!
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Enjoy a peaceful retreat on this serene beach, accessible by sailboat, with calm waters and a natural, undeveloped atmosphere.

Waterfront Lusby Retreat w/ Deep-water Dock & Slip

3.0 star property
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Waterfront House With Dock, Kayaks, & Sailboat!
Enjoy a serene view of the lush landscape from this room's window, featuring a table with a vase, candle, and tray.

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Enjoy cooking in this well-equipped kitchen with a large island, stovetop, and oven.

Waterfront Lusby Escape w/ Fire Pit & Kayaks!

3.0 star property
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
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!
Historic Hoopersville Getaway on Chesapeake Bay!
Enjoy meals in the kitchen and dining area, featuring an oven, microwave, and round table with floral-patterned chairs.

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!
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!
1915 Historic Cambridge Property w/ Fire Pit!
Relax by the fire pit surrounded by lush greenery and comfortable seating.

1915 Historic Cambridge Property w/ Fire Pit!

3.0 star property
1915 Historic Cambridge Property 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
Modern Solomons Cottage Rental - Walk to Island!
Relax in this stylish bedroom with a large bed, dresser, and wardrobe.

Modern Solomons Cottage Rental - Walk to Island!

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

Sleep Inn & Suites California MD

Sleep Inn & Suites California MD

10/10 Excellent
"Nothing super fancy here, but everything was clean, the bed was comfy, there were stocked vending machines and breakfast, and every employee I encountered greeted me and smiled. I would definitely stay here again."
Rachael 1-night trip
Posted 1 day ago
Sleep Inn & Suites California MD