Vacation rentals in Chance

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Top-rated vacation rentals in Chance

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Superhost

A bright dining area features a round table surrounded by wooden chairs. A colorful table runner adds a vibrant touch. Large sliding glass doors provide an unobstructed view of the water and open to an outdoor deck. A stylish chandelier hangs from the ceiling.

Home in Deal Island Historic District

4.88 out of 5 average rating, 8 reviews

Reel Relaxation-Waterfront

Reel Relaxation – A Waterfront Escape Nestled on Rock Creek in Chance, MD, Reel Relaxation offers stunning water views, a private dock, and a cozy fireplace. Unwind in the hot tub, gather by the fire pit, or enjoy fresh seafood on the screened porch. Kayak through Rock Creek or relax on the private beach just across the water with permission. With three bedrooms, a pull-out couch, and modern amenities, this retreat sleeps up to 9. Whether fishing, grilling, or unwinding, it's the perfect escape.

Top guest favorite

The sun is seen shining through the branches of a tree, casting rays of light over a calm river. The water reflects the sunlight, creating a sparkling effect. A wooden pier extends into the water, surrounded by lush greenery.

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 356 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Top guest favorite

A renovated home is situated against a vibrant sunset sky, with warm colors reflecting off the exterior. Large glass doors open to the view of the surrounding water. Adirondack chairs are arranged on the deck, offering a space for relaxation outdoors.

Home in Deal Island Historic District

4.97 out of 5 average rating, 60 reviews

"Promise Point" Bay front home with dock. 3BR 2BA

Take it easy at this unique and tranquil getaway. Open floor plan home completely renovated in 2022. Surrounded by water on 3 sides with dock access and neighbors a community beach and boat ramp. Great place for fishing, crabbing, boating, jet skiing, kayaking or just relaxing by the fire pit. 3BR 2BA with florida room surrounded by large decks, full kitchen with quartz countertops, washer and dryer, sleeps 12, 1 queen BR, 1 Full BR, Triple Bunk BR, queen Sleeper, futon, and twin roll away bed.

Guest favorite

A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.

Home in Deal Island Historic District

4.88 out of 5 average rating, 34 reviews

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!

Guest favorite

The charming exterior of the tiny cabin features wooden siding and a welcoming porch. Two decorative signs adorn the front door, and a pair of mushroom-shaped stools are placed on either side of the entrance. The view includes open fields and a clear blue sky.

Tiny home in Cambridge

4.89 out of 5 average rating, 607 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Superhost

Two chairs are positioned on sandy ground, facing a tranquil bay at sunset. Fishing poles stand upright in the sand beside the chairs, while soft waves reflect shades of orange and pink from the sky. A grassy area frames the scene, enhancing the peaceful atmosphere.

Cottage in Deal Island

4.64 out of 5 average rating, 238 reviews

Deal Island Bay Cottage - Maryland

Discover the charm of the Eastern Shore at the Deal Island Bay Cottage! Nestled on a spacious lot, it provides a peaceful escape with easy access to a Chesapeake Bay beach. Enjoy morning sunrises from the screened porch, Ideal for crabbing enthusiasts, the cottage includes local tips for the best spots. With high-speed WiFi and modern amenities, it’s perfect for both relaxation and remote work. Experience a true Waterman community and make lasting memories in this cozy retreat!

Guest favorite

The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.

Guest suite in Crisfield

4.76 out of 5 average rating, 215 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Top guest favorite

A rustic barn loft is nestled among trees, featuring a welcoming staircase leading to the upper deck. Soft lights illuminate the entrance, enhancing the natural surroundings. The gravel driveway and landscaped area provide convenient access to the property, highlighting its serene setting.

Loft in Hebron

5 out of 5 average rating, 105 reviews

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Top guest favorite

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

4.99 out of 5 average rating, 228 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Top guest favorite

A vibrant sunset casts a warm glow over the water, blending hues of orange, purple, and pink. Silhouetted pilings rise from the bay, while gentle waves reflect the colorful sky. A small dock is visible in the foreground, inviting guests to enjoy the serene view.

Guesthouse in Deal Island Historic District

5 out of 5 average rating, 34 reviews

Blue Crab Bungalow

Our charming bungalow allows you to relax, refresh and truly unwind while taking in views of the bay. Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach for swimming and public boat ramp are less than 5 minutes away. We are about an hour to Ocean City, Chincoteague, and Assateague.

Superhost

A private retreat is visible with two houses positioned along a sandy beach. A wooden pier extends toward the water. Lush green trees frame the property, providing a serene atmosphere. The main house features a spacious facade, while the guest house presents a charming design, both overlooking the waterfront.

Villa in Princess Anne

4.83 out of 5 average rating, 144 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse

Guest favorite

The exterior of the suite features a light-colored siding with brown shutters on either side of the door. A sturdy ramp and steps provide accessible entry. A small porch is visible in front, and the bright blue sky serves as a backdrop.

Guest suite in Deal Island Historic District

4.91 out of 5 average rating, 116 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.