Upper Hooper Island Vacation 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
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Upper Hooper Island Vacation Homes

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

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

10.0 out of 10, Exceptional, (50)
"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
Terrace/patio

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

9.8 out of 10, Exceptional, (130)
"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
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "
Waterfront Wildlife Retreat on the Patuxent River
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

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 $262
CA $565 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"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 $332
CA $648 total
includes taxes & fees
Aug 27 - Aug 28
Beautiful Waterfront Retreat in Cambridge!
Hoopers Island Retreat
WiFi, bed sheets

Hoopers Island Retreat

Hoopers Island Retreat
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

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

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

2.0 star property
8.4 out of 10, Very good, (6)
"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
Discover tranquility near Calvert Cliffs
Outdoor dining

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
Walk to Beach: Elegant Escape in Lusby!
Fridge, microwave, stovetop, dishwasher

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!
Stunning secluded Luxury waterfront cottage with private deep water pier!
Exterior

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!
Private Waterfront Home with Dock in Solomons, MD
Fridge, microwave, oven, stovetop

Private Waterfront Home with Dock in Solomons, MD

10.0 out of 10, Exceptional, (6)
"Nice and cozy"
Private Waterfront Home with Dock in Solomons, MD
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (11)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
The Blackwater refuge country house on a quiet 12 acres
Property grounds

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
Coastal Haven- Beach w/ BBQ
Beach towels

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, (3)
"Home was spacious, clean and comfortable. Walking distance to shops and restaurants. Quaint little town! Would highly recommend."
Near Solomons Island Boardwalk: Home w/ Hot Tub!
2 Mi to Lighthouse: Waterfront Home w/ Dock!
Interior

2 Mi to Lighthouse: Waterfront Home w/ Dock!

8.6 out of 10, Excellent, (36)
"Great location to downtown Solomons Island Center."
2 Mi to Lighthouse: Waterfront Home w/ Dock!
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio

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

9.8 out of 10, Exceptional, (69)
"Enjoyed the kayaks and paddle boards! The golf cart was great to use to take down to the water and back. Comfortable beds and super clean. Rick was very responsive and great yo work with. "
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
Fridge, microwave, oven, stovetop

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"Our group really enjoyed the house and the hospitality. There were several nice touches to make us feel welcomed."
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy
Riverside House w/ Kayaks, Piano & Fireplace
Fridge, microwave, stovetop, dishwasher

Riverside House w/ Kayaks, Piano & Fireplace

8.8 out of 10, Excellent, (15)
"Exploring via water on the kayaks was a beautiful way to see the area!! "
Riverside House w/ Kayaks, Piano & Fireplace
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

Holiday Inn Express & Suites Lexington Park-California by IHG

Holiday Inn Express & Suites Lexington Park-California by IHG

10/10 Excellent
"The breakfast bar included oatmeal, which was a treat for me -- I have oatmeal every morning at home. "
Mary 1-night trip
Posted 16 hours ago
Holiday Inn Express & Suites Lexington Park-California by IHG