Hoopers Island Vacation Rentals

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Nov 28 - Nov 29
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Dec 5 - Dec 7

Vacation Rentals in Hoopers Island

Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek
10.0 out of 10, Exceptional, (51)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Property grounds
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek
10.0 out of 10, Exceptional, (81)
"Beautiful location, so peaceful and quiet, we loved our stay! "
United States
Janna C.
Waterfront Cottage in Beautiful Hoopers Island
Exterior
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!

Church Creek
250 ACRE ESTATE ON CHESAPEAKE BAY, SLEEPS 40 W-AC VACATIONS, WEDDINGS] REUNIONS!
Property grounds
New Island Home on the Chesapeake Bay Sunsets

New Island Home on the Chesapeake Bay Sunsets

Church Creek
10.0 out of 10, Exceptional, (7)
"A well stocked and well kept house on the water with fantastic sunset views, a big yard for games, and a game room and fire pit for the night. "
United States
Charles D.
New Island Home on the Chesapeake Bay Sunsets
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Exterior
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

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

Drayden
9.8 out of 10, Exceptional, (77)
"Host was gracious. house is well prepared and clean. "
United States
Mark A.
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
$344 nightly
The price is $365
Dec 14 - Dec 15
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (37)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$254 nightly
The price is $269
Nov 30 - Dec 1
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby
10.0 out of 10, Exceptional, (63)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
United States
Whitney H.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Microwave, oven, stovetop, dishwasher
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"Stayed for business, completed our project and enjoyed some local eating spots. "
United States
Justin J.
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

Port Republic
10.0 out of 10, Exceptional, (181)
"Everything about this cabin was just what we were looking for! From the initial booking until we left we were taken care of by Brett. The pictures on-line were spot on but seeing the bay view in person from the windows and deck took my breath. There was a lot to do and we took advantage of close by activities (hiking, paddle-boarding, kayaking, jet skiing) but the cabin is a destination in itself with it's peaceful and calm surroundings. We were blessed with beautiful sunrises, hummingbirds and...
United States
Vicki K.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

Cambridge
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Fridge, microwave, oven, stovetop
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand

Point Lookout
10.0 out of 10, Exceptional, (125)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
United States
David Z.
Call to reserve last minute stay! Hideaway in Hays Beach: 1 Minute Walk to Sand
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Smart TV, fireplace, books, offices
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Beach
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
9.0 out of 10, Wonderful, (18)
"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."
United States
Christopher H.
Belle of the Chesapeake Bay
Outdoor dining
Discover tranquility near Calvert Cliffs

Discover tranquility near Calvert Cliffs

Saint Leonard
9.8 out of 10, Exceptional, (18)
"Comfortable beds, large house with awesome views…had a great experience"
United States
Deborah R.
Discover tranquility near Calvert Cliffs
Interior
Peaceful Waterfront Apartment in the Heart of Solomons Island

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Nice little place to stay"
United States
Eric S.
Peaceful Waterfront Apartment in the Heart of Solomons Island
Property grounds
Stunning Water Front Home with Private Dock and Beach and Sunsets

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby
10.0 out of 10, Exceptional, (26)
"Great place. Would definitely stay here again. "
United States
Joshua M.
Stunning Water Front Home with Private Dock and Beach and Sunsets
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Great amenities, excellent spa and service, friendly staff and great food."
Janet 1-night trip
Posted 3 days ago
Hyatt Regency Chesapeake Bay

Find out more about Hoopers Island

Everything you need to know about Hoopers Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hoopers Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hoopers Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Hoopers Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $269 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hoopers Island rentals

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

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.

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