Vacation rentals in Chance

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Top-rated vacation rentals in Chance

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Top guest favorite

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.

Cottage in Deal Island Historic District

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.

Top guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 348 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 driving tour map and welcome guide for the Harriet Tubman Underground Railroad State Park are displayed on a wooden surface. The map features prominent colors and outlines routes. The welcome guide has an image of flags flying in front of a red brick visitor center, with text indicating its relevance to the park.

Tiny home in Cambridge

4.98 out of 5 average rating, 200 reviews

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

Superhost

A rustic wooden bench is positioned against a gray corrugated wall, adorned with five chickens of various colors. Two hanging bird feeders are visible on the right, adding a charming touch to the farm setting.

Farm stay in Cambridge

4.78 out of 5 average rating, 374 reviews

Blackwater & Snakehead Farm "She Shed" Tiny House

The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, farm barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living on the farm!

Top guest favorite

Home in Crisfield

4.96 out of 5 average rating, 287 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Top guest favorite

Apartment in Lexington Park

5 out of 5 average rating, 383 reviews

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 food 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 fall, winter, spring, summer! SUNSETS!

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, 210 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

Two wooden adirondack chairs sit beside a stone fire pit, adorned with decorative pillows. A softly glowing fire captures attention as a rustic barn stands in the background, framed by lush greenery. The scene invites relaxation in a natural setting.

Loft in Hebron

5 out of 5 average rating, 103 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

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

4.99 out of 5 average rating, 227 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 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.

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 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, 105 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 favorite

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.

Guest suite in Deal Island Historic District

4.9 out of 5 average rating, 113 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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Popular amenities for Chance vacation rentals

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Top guest favorite

A welcoming porch features two turquoise rocking chairs placed on a wooden deck. A hanging planter with flowers adds a touch of color. The entrance is framed by double doors, and pebbles line the ground for a charming outdoor setting.

Tiny home in Parsonsburg

4.98 out of 5 average rating, 45 reviews

Cozy Cottage Hideaway

IratxeRating, 5 stars1 day ago

We fall in love with the place. We had a peaceful, relax and fun weekend. Ocean city is 20 min away by car.

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, 235 reviews

Deal Island Bay Cottage - Maryland

MichaelRating, 5 stars3 weeks ago

Great place to stay for the family fishing vacation. The house is clean, the neighborhood quiet and we were only a 1 minute from the docks. We had a great time and enjoyed staying at the house.

Guest favorite

A cozy seating area is featured on the porch, showcasing a wicker loveseat with bright yellow cushions. Natural light filters in through the nearby window, and the surrounding greenery offers a serene backdrop.

Home in Crisfield

4.96 out of 5 average rating, 52 reviews

Catch of the Bay

BrandonRating, 5 stars1 month ago

Felt like I was home even being away, love the town of Crisfield and this place made us feel safe and secure as well as very Comfortable. We will be back for another short stay again before summer ends.

Guest favorite

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

4.98 out of 5 average rating, 103 reviews

One of a kind waterfront home with private dock

ZoeyRating, 5 stars2 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! 😊

Top guest favorite

Two goats are positioned on a small white platform, displaying distinct black and brown fur. The goats stand against a backdrop of green grass and trees, with a wire fence delineating the area. The sky is clear and blue.

Loft in Pocomoke City

4.99 out of 5 average rating, 89 reviews

Cozy Barn Loft: Country Views & Central to Beaches

KristaRating, 5 stars2 weeks ago

We really enjoyed our stay at the loft! It was right like the pictures and it was very clean. the farm fresh eggs were a fun touch! :) The fun little touches, like the snacks on the table, the eggs in the fridge and the binder of local things to do were really appreciated! highly recommend this place!

A porch area is showcased, featuring two red chairs positioned around a stone fire pit. The view extends to a private dock across a bay, surrounded by grassy landscape, under a clear sky.

Cottage in Deal Island Historic District

5 out of 5 average rating, 5 reviews

Waterfront Maryland Retreat w/ Dock & Bay View!

JosephRating, 5 stars10 months ago

There is not a lot go say about this location except if you are looking for heaven then you may have found it. Deal Island is one of the most peaceful and unplugged places on earth. The home is right on the Chesapeake Bay and we as a family spent countless hours crabbing and sunbathing on the dock. We also went to the beach as well for paddleboarding and beach time. This home defines perfect bay side accommodations and let's you unplug from the daily world just by stepping in to it. I will never forget this vacation and Deal Island is a place in which this world needs more of. Great host(evolve and the owner) and answered every question I needed. Can't wait to go back.

Guest favorite

A bright and airy bathroom features a white soaking tub complemented by a wooden tray. A potted plant adds greenery, while a plush rug lies on the marble floor. Light filters in through a small window, and decorative art pieces adorn the walls.

Home in Princess Anne

4.93 out of 5 average rating, 14 reviews

countryside home in Princess Anne

AlexisRating, 5 stars1 week ago

Katlynn was a phenomenal host, she was quickly responsive whenever I had a question and was super flexible with me and my stay. If you’re looking for something peaceful and to feel right on at home, this is the place to go.

Guest favorite

A modern bathroom features three round mirrors above a double sink vanity with brushed metal faucets. The space incorporates navy blue cabinetry and light-colored stone countertops. A separate shower area is visible, with a textured wall and wooden bench, on the right side of the image.

Boat in Kinsale

5 out of 5 average rating, 8 reviews

Spend the Night on the River

AngelaRating, 5 starstoday

What a fun, non traditional location for an overnight. Loved being on the water and close to the activities at The Slips. Annie was great at communication. Can’t wait to stay again.

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Vacation rentals in Chance

Top-rated vacation rentals in Chance

Vacation rentals for every style

Popular amenities for Chance vacation rentals

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