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Get away home for the winter on the Chesapeake Bay

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

Year Round Playground - Rare Rustic-Modern Getaway

WINTER SALE 10%!! Feeling the fall & winter blues stuck in cramped city life? IMAGINE YOURSELF with a cup of hot cocoa surrounded by foliage, roasting s'mores by fire pit, enjoying hot tub under the stars feeling one with nature! Experience the magic of Eastern Shore in a one-of-a-kind waterfront retreat with a private dock on East Creek! This peaceful 3BR/2.5BA getaway offers the perfect mix of privacy and cold-weather comfort. Only missing piece is YOU! BOOK NOW & be the family vacation HERO!!

Marshall’s Retreat Chesapeake small town getaway

Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs.

Countryside Home in Princess Anne

Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

Waterfront Marion Station Retreat w/ Private Dock!

Escape to ‘Sunsets Waiting,’ a dreamy 3-bedroom, 3-bath vacation rental on the shores of Colbourn Creek. Explore nearby attractions, like the picturesque Janes Island State Park for kayaking, crabbing, and fishing adventures, or stop by Tangier Island Cruises for a relaxing boat tour. After a day of outdoor fun, gather around the fire pit and enjoy a cookout on the charcoal grill. With a private dock, you can easily access the pristine waters for fishing or crabbing excursions. Book now!

Mary’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Mary’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. You simply won’t want to leave! A 30 minute drive to Chesapeake Bay and about 45 minutes to Chincoteague Island There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Martha's Cottage” (check my profile for listing).

Chalet Style Home, private country setting

Crooked Elm Cottage, nestled in Somerset County on Maryland's lower Eastern Shore, is ideal for outdoor enthusiasts. With easy access to the Chesapeake Bay and Atlantic Ocean, guests can enjoy birdwatching, hiking, fishing, boating, and biking, making it the ultimate base for adventure. Fully renovated, this charming retreat features a modern kitchen, a spacious living/dining area, high-speed internet, two expansive decks, and an outdoor recreation room complete with a pool table.

Bay Beauty with boat slip & waterfront views!

Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!

House of the Setting Sun/Deal Island Bayfront Home

Soak up the quiet beauty of Tangier Sound at this bayfront getaway with stunning sunset views among the pines. Enjoy crabbing, fishing, and swimming off the dock. Dive into nature photography, birdwatching, hunting, kayaking in the wetlands, and more. There's a small local beach less than 5 minutes away. It's far enough away to unplug, but less than an hour to Ocean City, Chincoteague, and Assateague. And there's plenty to enjoy onsite, including sunsets 9 months out of the year!

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Crisfield Cabin by Homelystay

Escape to a serene retreat, perfect for family relaxation. Nestled on five acres with a picturesque pond, this charming cabin features four bedrooms, two full baths, a cozy living room with a fireplace, a breakfast nook, and a spacious dining room with a large table for gatherings. Enjoy peaceful views from the picture windows overlooking the pond. Conveniently located just a few miles from shopping and amenities, offering both privacy and accessibility.

Waterfront Historic Gem w/ Kayaks & Fire Pit

Experience the charm of The 1850 House, a 4-bedroom riverside getaway in historic Quantico, MD. Nestled along the Wicomico River, this pet-friendly retreat comes with kayaks, paddleboards, bikes, and a fire pit for outdoor adventures. Start your mornings on the furnished deck, explore nearby parks, beaches, and trails, or unwind in the screened porch and fenced yard. With a dedicated workspace, it’s a perfect blend of relaxation and convenience.