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Hoopers Island Vacation Rentals

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Our top choices for Hoopers Island vacation rentals

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is CA $647
CA $1,297 total
includes taxes & fees
Jul 1 - Jul 2
'the Bayside Escape' Remote Chesapeake Bay Estate

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 reviews)
"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 CA $383
CA $462 total
includes taxes & fees
Jun 29 - Jun 30
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 review)
"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 CA $383
CA $462 total
includes taxes & fees
Jun 29 - Jun 30
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
The price is CA $544
CA $1,315 total
includes taxes & fees
Jul 5 - Jul 6
'The Bayside Escape' Remote Chesapeake Bay Estate

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is CA $778
CA $1,624 total
includes taxes & fees
Jun 30 - Jul 1
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (132 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is CA $497
CA $940 total
includes taxes & fees
Jul 19 - Jul 20
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (52 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is CA $220
CA $456 total
includes taxes & fees
Jul 13 - Jul 14
Soul Oasis - home on the Chesapeake Bay

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is CA $637
CA $1,080 total
includes taxes & fees
Jul 7 - Jul 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (12 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is CA $656
CA $1,225 total
includes taxes & fees
Jul 5 - Jul 6
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $710
CA $1,388 total
includes taxes & fees
Jun 29 - Jun 30
4-BR Waterfront Turret Home

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (16 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is CA $291
CA $585 total
includes taxes & fees
Jul 15 - Jul 16
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (13 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is CA $599
CA $1,068 total
includes taxes & fees
Jul 8 - Jul 9
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is CA $660
CA $1,649 total
includes taxes & fees
Jun 29 - Jun 30
Lakefront Cabin near Solomons Island w/ Hot Tub

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, (12 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
The price is CA $522
CA $891 total
includes taxes & fees
Jul 5 - Jul 6
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (34 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is CA $220
CA $361 total
includes taxes & fees
Jul 5 - Jul 6
Sailwinds Loft at Cambridge Creek

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

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
The price is CA $390
CA $727 total
includes taxes & fees
Jul 28 - Jul 29
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $226
CA $400 total
includes taxes & fees
Jul 13 - Jul 14
Deal Island Bay Cottage

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (44 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is CA $653
CA $824 total
includes taxes & fees
Jul 13 - Jul 14
Sunset Breezes - quiet waterfront retreat

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is CA $566
CA $1,162 total
includes taxes & fees
Jul 15 - Jul 16
Brand New Waterfront Home • Marina Views • Walk Downtown & Events • Sleeps 8

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (23 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is CA $376
CA $710 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hoopers Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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