Hoopers Island Holiday Rentals

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Our top choices for Hoopers Island holiday rentals

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is AU$494
includes taxes & fees
27 Dec - 28 Dec
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is AU$494
includes taxes & fees
27 Dec - 28 Dec
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7)
The price is AU$401
includes taxes & fees
25 Jan - 26 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is AU$423
includes taxes & fees
5 Jan - 6 Jan 2026
Soul Oasis - home on the Chesapeake Bay

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is AU$422
includes taxes & fees
1 Jan - 2 Jan 2026
Deal Island Bay Cottage

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (8)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is AU$480
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is AU$532
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is AU$532
includes taxes & fees
12 Jan - 13 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is AU$440
includes taxes & fees
6 Jan - 7 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is AU$542
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is AU$310
includes taxes & fees
6 Jan - 7 Jan 2026
Tangier Escape, great place get away from it all on Deal Island, MD.

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is AU$562
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is AU$384
includes taxes & fees
29 Dec - 30 Dec
Sailwinds Loft at Cambridge Creek

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Port Republic
9.4 out of 10, Exceptional, (6)
"I was traveling for work and this was a perfect spot to stay for me. "
United States
Tyler B.
The price is AU$266
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD

Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Smith Island
9.8 out of 10, Exceptional, (15)
"Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful. "
United States
Debra M.
The price is AU$437
includes taxes & fees
31 Dec - 1 Jan 2026
Come escape to Smith Island for the winter and enjoy nature, peace and quiet

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
2.0 star property
Solomons
10.0 out of 10, Exceptional, (7)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
United States
Rudy L.
The price is AU$1,132
includes taxes & fees
1 Jan - 2 Jan 2026
4-BR Waterfront Turret Home

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
The price is AU$516
includes taxes & fees
30 Dec - 31 Dec
Sunset Breezes - quiet waterfront retreat

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$586
includes taxes & fees
4 Jan - 5 Jan 2026
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is AU$1,349
includes taxes & fees
4 Jan - 5 Jan 2026
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is AU$590
includes taxes & fees
25 Jan - 26 Jan 2026
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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

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$423 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.