Vacation rentals in Chance

Cottage in Deal Island Historic District

A bright yellow umbrella provides shade over a red table surrounded by two tall blue chairs and two yellow chairs on a wooden deck. The deck overlooks the waterfront with grassy areas and a pier visible in the distance.

4.94 out of 5 average rating, 16 reviews

Cozy "Waterfront Cottage"

Waterfront cottage located on Tangier Sound. Sleeps 6. One Bedroom with queen size bed and queen size pull out sofa in Living Room; queen size pull out sofa in the Sun Room; 1 Bathroom with walk in shower, Kitchen fully stocked with utensils, pots/pans, dishes/appliances, Living Room, Spacious Sun Room, Large open deck, with private pier. Enjoy fishing and crabbing directly off the pier and enjoy drinks and dinner on the spacious open deck. Public boat ramp is 2 miles away with public beach.

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 352 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.

A bright Florida room is displayed with large windows offering water views. Comfortable seating includes navy blue chairs and a white coffee table. A wooden dining table is surrounded by white chairs. A light-colored area rug depicts a leaf pattern, adding to the coastal ambiance.

4.97 out of 5 average rating, 59 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.

5 out of 5 average rating, 21 reviews

A historic church with a tall steeple is depicted alongside a plaque detailing Smith Island's history. The building features arched stained-glass windows and a brick base. Nearby, white houses with picket fences and American flags are visible against a cloudy sky.

Home in Smith Island

Discover Smith Island! (But breakfast first)

Welcome to The Ungovernable Goose! My name is Luci, but my dad called me "Goose", and I've always been a bit of a rebel. The philosophy here is simple: Do whatever brings you joy! Stay up late. Sleep in. Take naps. Eat the cake. Drink the good stuff. Speak your mind. Live fiercely. Read banned books. Go barefoot. Spark a revolution. Become ungovernable... Let us help you discover all of the history, culture and natural beauty Smith Island has to offer. Recreation Packages Available!

A bright sunroom features a cozy window seat adorned with soft cushions and decorative pillows. Natural light floods in through multiple windows, while a simple wreath decorates the door. The light blue walls and wooden accents create a calm, inviting space.

4.94 out of 5 average rating, 32 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!

Superhost

The image displays a serene sunset over a body of water, with the sun positioned low on the horizon. Silhouettes of trees and vegetation can be seen along the far shore, contrasting against the warm hues of orange and pink in the evening sky.

Guest suite in Crisfield

4.75 out of 5 average rating, 212 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.

4.97 out of 5 average rating, 30 reviews

Rusty Anchor

Escape to the Rusty Anchor, a beautifully restored 1900s farmhouse on Deal Island, MD! With 3 cozy bedrooms, it's perfect for families or friends. Just around the corner, enjoy a cozy beach, crabbing, and easy access to fishing (Redfish, Striped Bass, Flounder) and waterfowl hunting. Only a 5-minute bike ride to beaches and boat ramps. Book now and receive a link to our store to reserve add-ons or schedule special experiences for your stay!

5 out of 5 average rating, 103 reviews

A rustic wooden table features a plate of oysters and a bottle of red wine, accompanied by a glass filled with wine. A fire pit emits a warm glow nearby, with the scenic view of a creek and trees in the background.

Loft in Hebron

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.

4.99 out of 5 average rating, 227 reviews

A wooden boardwalk extends toward a sandy beach, flanked by tall grasses and wetlands. The peaceful water is visible in the distance under a clear blue sky, with a few clouds adding texture to the scene.

Cottage in Westover

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.

Guesthouse in Deal Island Historic District

A sandy beach stretches alongside calm waters, framed by gentle grasses on either side. A pier can be seen in the distance, with a few figures walking leisurely along the shore under a soft sunset sky.

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 serene riverside scene captures the calm waters reflecting the sky. A sandy beach area leads to a wooden pier extending into the water. Lush grass and a few wooden posts add natural elements to the picturesque landscape.

Cottage in Tyaskin

4.86 out of 5 average rating, 107 reviews

Charming Cottage in Tyaskin, MD

Charming New England salt box style cedar sided cottage directly across from Tyaskin Park. The Cottage is larger inside than appears on the exterior due to vaulted ceilings in the living room, kitchen/ dining areas. Beautiful views of the Nanticoke river from the living room, dining area and large deck. Pine flooring in all rooms with the exception of the tile floor bath and carpeted loft.

Guest suite in Deal Island Historic District

A spacious wrap-around deck features a wooden picnic table and a charcoal grill, enhancing outdoor dining options. A lounge chair is positioned nearby, creating an inviting spot for relaxation. The deck's wooden flooring extends along the side of the house, with a view of the surrounding greenery.

4.9 out of 5 average rating, 114 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.

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Other great vacation rentals in Chance

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, 236 reviews

Deal Island Bay Cottage - Maryland

AshRating, 5 stars1 week ago

Great location. Very rural, quiet neighborhood, very responsive host.

4.84 out of 5 average rating, 73 reviews

A collection of bicycles is positioned within a storage space. A blue bicycle with a mesh basket is prominently featured in the foreground, while two other bicycles can be seen behind it. The setting is organized with wooden flooring visible beneath the bikes.

Cottage in Wingate

Blue Crab Cottage: Remote+Nature+Fishing+Views

DianeRating, 5 stars3 days ago

We had a wonderful stay at Blue Crab Cottage. The house was peaceful with beautiful breezes. It was comfortably decorated with plenty of space for the eight of us. The screened in porch off the deck that was an excellent surprise. There is also an eastern shore style peer right next to the house that led into the marsh where the kids enjoyed crabbing. We had a great time sitting outside and enjoying the beautiful marsh landscape. Jody was a great hos. she was responsive and answered all of our questions.

A bright and spacious living area features a cozy sofa with colorful cushions and a coffee table in the center. A modern fireplace stands against a white shiplap wall, while large windows allow natural light to fill the room. Decorative shelves showcase books and personal items.

4.83 out of 5 average rating, 6 reviews

Reel Relaxation-Waterfront

CrystalRating, 5 stars5 days ago

The location was very beautiful. It fit our family of 6 comfortably. I appreciate the air conditioning and how cool it felt from the hot temps outside. There was lots of wood already available to make a fire, hot tub was ready to use, lots of available items already in the house for use. Anything you could want or need, she basically had. It’s also accessible to day trips near by - about an hour or so to the beaches. Very secluded and peaceful.

5 out of 5 average rating, 47 reviews

Home in Heathsville

Northern Neck Creek Retreat w/ king suite, firepit

JulietteRating, 5 stars1 month ago

Creek Retreat is a perfect place to kick back and relax. Surrounded by nature, a private oasis. The space is well appointed, clean and comfortable. Tastefully decorated. Added amenities and attention to details elevate the experience. Enjoy kayaking and sitting by the fire. Georgia is a great hostess and is proactive and responsive. If you're looking for a getaway, book it here!

Superhost

A serene view of the water at sunset, with soft waves gently lapping at the shore. The horizon displays a warm gradient of colors as the sun sinks, reflecting beautifully on the surface of the water.

Home in Westover

4.94 out of 5 average rating, 82 reviews

Beachfront Chesapeake Bay Retreat

MarvinRating, 5 stars3 weeks ago

Me encantó muy cómodo bonita la playa y organizado se los recomiendo

4.98 out of 5 average rating, 103 reviews

A modern kitchen space is showcased with a polished granite countertop and a sleek faucet. The window allows natural light to illuminate the area, while decorative items, including a crab figure, enhance the coastal theme. Clean lines and a subtle colour palette contribute to the overall aesthetic.

Home in Quantico

One of a kind waterfront home with private dock

ZoeyRating, 5 stars4 weeks ago

This was one of my favorite stays so far! The location was quiet and peaceful with beautiful views all around. The dock in the backyard was nice, my dogs loved the fenced in yard and big yard to the side of the house. The house was clean and the bed was super comfortable. I can’t wait to come back! 😊