Upper Hooper Island Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Upper Hooper Island

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$663
includes taxes & fees
13 Oct - 14 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
Fridge, microwave, oven, stovetop

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10.0 out of 10, Exceptional, (193)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (258)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (123)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
El Camino
Terrace/patio

El Camino

10.0 out of 10, Exceptional, (49)
"Awesome location and accommodations. Very clean and comfortable. "
El Camino
Sailwinds Loft at Cambridge Creek
Private kitchen

Sailwinds Loft at Cambridge Creek

10.0 out of 10, Exceptional, (15)
"The location and apartment were perfect. "
The price is NZ$438
includes taxes & fees
23 Oct - 24 Oct
Sailwinds Loft at Cambridge Creek
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Exterior

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

9.8 out of 10, Exceptional, (75)
"What a great property, wildlife abounds!!! We had a fantastic weekend with family and friends!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

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

10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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, (55)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Solomons Apartment
Interior

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is NZ$459
includes taxes & fees
8 Oct - 9 Oct
Waterfront Solomons Apartment
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (79)
"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
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun-loungers, beach towels

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.
High River Bank with $1M Sunset View, 3 min to College
Terrace/patio

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (2)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
The price is NZ$726
includes taxes & fees
6 Oct - 7 Oct
High River Bank with $1M Sunset View, 3 min to College
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (16)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
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, (15)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

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

8.8 out of 10, Excellent, (5)
"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 NZ$509
includes taxes & fees
20 Oct - 21 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
Dining

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

9.4 out of 10, Exceptional, (3)
"Very beautiful property with clean rooms. Very responsive property management. Unfortunately the Outdoor grill and the dock light was not functional and the owner did bot resolve it during our stay. Hopefully they will take care of them before the next guest arrives."
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou
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

Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

10/10 Excellent
"Everything was clean. Well-designed interior. Good security and lighting. Ample parking. Nice breakfast."
Paula 1-night trip
Posted 2 days ago
Days Inn & Suites by Wyndham Cambridge

Find out more about Upper Hooper Island

Find out more about Upper Hooper Island

Everything you need to know about Upper Hooper Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upper Hooper Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upper Hooper Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upper Hooper Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upper Hooper Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upper Hooper Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upper Hooper Island holiday rentals we have selected for you start as low as NZ$438 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Upper Hooper Island rentals

At Expedia, we put the best Upper Hooper Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upper Hooper Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upper Hooper Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upper Hooper Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia