Hoopers Island Holiday Rentals

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Holiday Rentals in Hoopers Island

Our top choices for Hoopers Island holiday rentals

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (78)
"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

Single family home with screened porch.

10.0 out of 10, Exceptional, (13)
"The house was very nicely done and extremely well stocked and the host was very friendly and super easy to deal with. We especially like the location for sunrise walks with the dogs and easy access to the national parks. "
Single family home with screened porch.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (49)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

10.0 out of 10, Exceptional, (64)
"An amazing family getaway. Laura was beyond wonderful and gracious. Laura took my family fishing and they cannot wait to do it again. People are friendly and wave as you pass them by. Food was great. Thank you to the owners of Old Salty’s who were kind to us. The view the food the drinks…top notch. The house had everything we needed. Would go again!!! "
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!

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 AU$535
includes taxes & fees
29 Sept - 30 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

10.0 out of 10, Exceptional, (192)
"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

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

10.0 out of 10, Exceptional, (11)
"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)

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"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

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

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

10.0 out of 10, Exceptional, (122)
"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

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

9.8 out of 10, Exceptional, (74)
"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

El Camino

10.0 out of 10, Exceptional, (48)
"Awesome location and accommodations. Very clean and comfortable. "
El Camino

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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 AU$654
includes taxes & fees
7 Oct - 8 Oct
High River Bank with $1M Sunset View, 3 min to College

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

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

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Waterfront property with private boat ramp and new dock!

9.2 out of 10, Wonderful, (16)
"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!
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 Hoopers Island Hotel Reviews

Find out more about Hoopers Island

Find out more about Hoopers Island

Everything you need to know about Hoopers 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 Hoopers 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 Hoopers Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hoopers Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hoopers 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hoopers 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 Hoopers Island holiday rentals we have selected for you start as low as AU$535 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hoopers Island rentals

At Expedia, we put the best Hoopers 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 Hoopers 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 Hoopers 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 Hoopers 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.