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Browse Select Hoopers Island Cottages

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The most well stocked property we've ever stayed! everything from extra phone chargers to blankets, tons of games and the kitchen as well."
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
Walk to Beach: Charming Maryland Home w/ Yard!

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace

Beachy Maryland A-frame: Steps to Chesapeake Bay!

3.0 star property
Beachy Maryland A-frame: Steps to Chesapeake Bay!

Pet-friendly Smith Island Cottage w/ Golf Cart!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
Pet-friendly Smith Island Cottage w/ Golf Cart!

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

3.0 star property
Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Sunrise Views: Waterfront Lusby Home w/ Deck!

3.0 star property
Sunrise Views: Waterfront Lusby Home w/ Deck!

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!

Screened Patio, Deck & Grill: Saint Inigoes Home!

3.0 star property
Screened Patio, Deck & Grill: Saint Inigoes Home!

Historic Hoopersville Getaway on Chesapeake Bay!

3.0 star property
Historic Hoopersville Getaway on Chesapeake Bay!

1 Mi to Boat Ramp: Peaceful Deal Island Home!

3.0 star property
1 Mi to Boat Ramp: Peaceful Deal Island Home!

Bay Views & Fire Pit: Taylors Island Retreat

3.0 star property
Bay Views & Fire Pit: Taylors Island Retreat

1915 Historic Cambridge Property w/ Fire Pit!

3.0 star property
1915 Historic Cambridge Property w/ Fire Pit!

Private Beach & Fishing Pier: Wicomico River House

3.0 star property
Private Beach & Fishing Pier: Wicomico River House

Modern Solomons Cottage Rental - Walk to Island!

3.0 star property
Modern Solomons Cottage Rental - Walk to Island!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & 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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