Holiday rentals in Hoopersville

Sunrise Waterfront Cottage

Enjoy the quiet and serenity of Hoopers Island from our cozy waterfront cottage. Take a break from the hustle and bustle of day-to-day life in this little town. Set up some chairs on the dock of the pier and fish or crab or catch some sun! Take a swim, kayak or float off the pier. Enjoy the sunrise relaxing on the back porch; sip your morning coffee or pick some local crabs on the back porch. Take a short walk down to the bridge to explore the small shoreline to collect shells and sea glass!

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Saltara

Welcome to Saltara – A Peaceful Family Escape on the Bay Saltara is where your family can slow down, reconnect, and experience the beauty of nature together. Nestled along the quiet shores of the Chesapeake Bay, this serene retreat offers breathtaking sunrises, and wide-open space for kids to explore freely. Start your mornings with coffee in the hammock, take a stroll by the water, or fire up the grill for an easy family meal. Take a warm outdoor shower is a must experience, portable potties.

Where the Road meets the Bay

Picture a secluded open concept 3 bedroom house on an island overlooking the Chesapeake Bay. Elevated home with a wraparound deck offering panoramic views. Large windows flood the interior with natural light showcasing sunsets that paint the sky with vivid hues. A telescope is provided for bird watching & observing their daily activities. The tranquil sound of water lapping against the shore enhances the serenity. This is a retreat designed for peace, reflection, and awe-inspiring moments.

Bay-“View” Peaceful, Scenic, Enjoy Crabs N Fish

Welcome to our unique water view home by the bay. Everyone here on Hoopers Island is very friendly and like family. Watch the local waterman as they come in with their catch!. Where fresh crabs, soft crabs, fish n oysters are plentiful!!!! All seafood is local and caught that morning right off the boat!! Having a memorable experience is what its all about. Where you can catch your own crabs and fish. Osprey, bald eagles, Heron and wildlife are plentiful!! It’s peaceful, relaxing and scenic!!

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Designer owned Coastal getaway retreat

Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away.

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here year around! SUNSETS!

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).