Upper Hooper Island Holiday 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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Upper Hooper Island

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

9.8 out of 10, Exceptional, (129)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (71)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"What a wonderful area on the water. The proprietors were such friendly and accommodating people. The apartment was clean and well stocked. They had a wide range of activities on the property. It was wonderful being able to sit near the water and enjoy my friend’s company. I highly recommend this welcoming place. "
Family and Pet-Friendly, Waterfront with Pier

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 AU$775
includes taxes & fees
8 Sept - 9 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (10)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is AU$450
includes taxes & fees
5 Sept - 6 Sept
Waterfront Solomons Apartment

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

9.6 out of 10, Exceptional, (29)
"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (31)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

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 AU$764
includes taxes & fees
13 Aug - 14 Aug
Beautiful Waterfront Retreat in Cambridge!

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is AU$467
includes taxes & fees
11 Aug - 12 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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!

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (9)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

Casa Maria heart of downtown Cambridge Maryland

9.8 out of 10, Exceptional, (10)
"Place was quiet and clean. Few minutes drive from the center of town. Definitely a great experience!"
The price is AU$283
includes taxes & fees
26 Aug - 27 Aug
Casa Maria heart of downtown Cambridge Maryland

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!
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

Top Upper Hooper Island Hotel Reviews