Upper Hooper Island Vacation Rentals

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Check prices for these dates

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

Browse Select Upper Hooper Island Vacation Homes

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $388
CA $701 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Relax on the spacious deck with a wicker sofa, cushioned chairs, and a hammock, perfect for unwinding in a serene atmosphere.

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (69)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Wildlife Retreat on the Patuxent River
Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Beautiful Waterfront Retreat in Cambridge!
Relax in this cozy room with a bar area featuring a large window offering a view of the outdoors.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (42)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $355
CA $681 total
includes taxes & fees
Aug 3 - Aug 4
Beautiful Waterfront Retreat in Cambridge!
The Blackwater refuge country house on a quiet 12 acres
Relax in a tranquil setting under the gazebo's open design with a sloped roof.

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (10)
"Very happy with this place, quiet, clean, all good. "
The Blackwater refuge country house on a quiet 12 acres
Screened Patio, Deck & Grill: Saint Inigoes Home!
Enjoy al fresco dining with a view of the surrounding landscape from this outdoor space featuring a table and chairs.

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.6 out of 10, Exceptional, (7)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!
4BDRM River front house with Private Beach in Hollywood
Relax in Adirondack chairs on the dock, overlooking the serene water and surrounding trees.

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (10)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Your private beach retreat in historic St. Mary's
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, oven, and dishwasher.

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (27)
"This was the perfect house for our family trip to St. Mary's -- nicely upgraded, well stocked and beautiful views. Will definitely return."
Your private beach retreat in historic St. Mary's
Waterfront Getaway with Dock
Compact kitchen with a sink, toaster, microwave, oven, and refrigerator.

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is CA $318
CA $386 total
includes taxes & fees
Aug 3 - Aug 4
Waterfront Getaway with Dock
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Relax in comfort under a striped umbrella, surrounded by the soothing sounds of the sea.

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (72)
"We had a great time. Private beach, spacious house, kayaks!"
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Coastal Haven- Beach w/ BBQ
Surrounded by a serene beach and calm waters, this tranquil setting features a majestic tree trunk.

Coastal Haven- Beach w/ BBQ

10.0 out of 10, Exceptional, (15)
"This house is amazing on a nice quiet street. We enjoyed our stay as it felt like we were home. Clean and cozy a lot of extra room we will be back next year for sure."
Coastal Haven- Beach w/ BBQ
Near Solomons Island Boardwalk: Home w/ Hot Tub!
Outdoor spa tub

Near Solomons Island Boardwalk: Home w/ Hot Tub!

10.0 out of 10, Exceptional, (1)
"The house was absolutely beautiful and the customer services was awesome! It is a very welcoming house that felt like home. The photos don't do it justice. It is very spacious!"
Near Solomons Island Boardwalk: Home w/ Hot Tub!
Private 9 acre Family Retreat on the Chesapeake Bay
Relax in this spacious living room with a high ceiling, featuring a large sliding glass door leading to an outdoor patio with a view.

Private 9 acre Family Retreat on the Chesapeake Bay

10.0 out of 10, Exceptional, (11)
"House was loaded with activities for all ages. So much to do and see. Host was outstanding! Friendly and extremely accommodating."
Private 9 acre Family Retreat on the Chesapeake Bay
Stunning Water Front Home with Private Dock and Beach and Sunsets
Guests can enjoy a serene waterfront experience from the Adirondack chair at the end of the pier.

Stunning Water Front Home with Private Dock and Beach and Sunsets

10.0 out of 10, Exceptional, (24)
"The property is perfect for family gatherings "
Stunning Water Front Home with Private Dock and Beach and Sunsets
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Relax on the covered porch with a sofa, bench, and table, surrounded by a beautiful view.

Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

2.0 star property
9.4 out of 10, Exceptional, (6)
"We enjoyed our stay at this lovely home. We liked the private, open land and private dock and lake. We swam in the lake which was super fun but we felt stinging and got rashes and realized the next day that there were jelly fish so beware before you go it to look out for them. The paddle boats were fun but one of them was a little broken and only went in circles. The Ranger was really fun to drive and ride in but it stalled the second day. The fire pit was really nice and we enjoyed riding our...
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Discover tranquility near Calvert Cliffs
Relax on the lakeside deck with a table and four chairs, surrounded by lush greenery and a serene atmosphere.

Discover tranquility near Calvert Cliffs

9.8 out of 10, Exceptional, (16)
"Comfortable beds, large house with awesome views…had a great experience"
Discover tranquility near Calvert Cliffs
Stunning secluded Luxury waterfront cottage with private deep water pier!
Surrounded by a serene forest, this two-story retreat offers a cozy balcony and a peaceful ambiance.

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (79)
"This property was exactly as described. The owner was very easy to work with. Unfortunately, we did not get to use the fire pit as it was rainy and cold. I would 100% stay here again."
Stunning secluded Luxury waterfront cottage with private deep water pier!
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Stylish hallway with white doors and a small table and chair.

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
8.0 out of 10, Very good, (5)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
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

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"Awesome Huge and Clean Pool!"
Leanna 2-night trip
Posted 3 days ago
Solomons Inn Resort & Marina