Hoopers Island Vacation Rentals

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Vacation Rentals in Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island
Surround yourself with nature's serenity by the tranquil water's edge, where a fire pit and wooden dock await.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"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
Historic Hoopersville Getaway on Chesapeake Bay!
Enjoy cooking in this well-equipped kitchen with a central island, modern appliances, and a large window offering a view of the outdoors.

Historic Hoopersville Getaway on Chesapeake Bay!

9.8 out of 10, Exceptional, (12)
"I really can’t say enough about this place! The house has so much charm! The island is very quiet! Great place to just get away and spend quality time with your family! Can’t wait to go back!"
Historic Hoopersville Getaway on Chesapeake Bay!
The Schultz Estate
Relax in the covered patio area with comfortable seating and a barbecue grill, surrounded by lush greenery and large windows.

The Schultz Estate

7.0 out of 10, Good, (21)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Relax on the lakeside with Adirondack chairs and tables, surrounded by open grasses and a serene lake view.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (48)
"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.
Cottage on the Bay
Relax in a serene outdoor space with a table and chairs, surrounded by large windows offering a view of a lush field and trees.

Cottage on the Bay

9.8 out of 10, Exceptional, (7)
"good place to fish good place to enjoy with family quiet and very clean place"
Cottage on the Bay
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
Relax outdoors with a picnic table and comfortable seating on the deck.

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

10.0 out of 10, Exceptional, (63)
"A wonderful long weekend getaway on Hoopers Island--close to the bay and to the attractions of the island. Laura is a great host who ensured we had everything we needed for our stay--a roomy house with a great screened in gazebo and plenty of activities for our elementary school aged kids. Highly recommend it!"
BEAUTIFUL PEACEFUL, SCENIC, ENJOY CRABS N FISH MEMORABLE, FREE TOUR OF AREA!
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Relax on the deck with ocean views, featuring a table and chairs.

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

10.0 out of 10, Exceptional, (177)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

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

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Historic home on Smith Island w/ dock!
Enjoy serene views of the calm water from the dock, surrounded by a peaceful shoreline.

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"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!
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (129)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Enjoy cooking in this well-equipped kitchen with a double oven, large refrigerator, and shelf.

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

10.0 out of 10, Exceptional, (117)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Stylish entrance with a wooden staircase and a mailbox.

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

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Maryland Vacation Rental w/ Private Pool & Dock
Enjoy meals al fresco on this deck surrounded by lush greenery.

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

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

10.0 out of 10, Exceptional, (120)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Enjoy cooking in this well-equipped kitchen with a central island and dining area.

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

9.6 out of 10, Exceptional, (29)
"Very roomy and lots of amenities. Superb location and private. Easy check-in and check-out. Guest contact was awesome - very responsive! Thanks so much!"
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront Wildlife Retreat on the Patuxent River
Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Solomons Apartment
Enjoy a marina view from the bay window, featuring a glass-top table and chair.

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (10)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is ￥23,554
￥42,977 total
includes taxes & fees
Sep 5 - Sep 6
Waterfront Solomons Apartment
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ￥39,890
￥73,917 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
Relax in a stylish space with a plush sofa, dining area, and large window.

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (31)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
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

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick

10/10 Excellent
"The owners are really working hard to make improvements to this property. The check-in was quick with a friendly staff. The rooms are receiving upgrades, and the breakfast has improved from my previous stays. For the price, it is difficult to beat the deal. "
William 2-night trip
Posted 2 days ago
SureStay by Best Western Prince Frederick