Vacation rentals in Chesapeake City

5 out of 5 average rating, 122 reviews

A cozy living area features a stone wall accentuated by natural light from multiple windows. Two upholstered armchairs and a sectional sofa are arranged around a fireplace, which is complemented by a mounted television above a wooden shelf. A floor lamp stands nearby.

Barn in Quarryville

The Barn at Locustwood Farm

Come enjoy your stay in our 1900 sq ft 19thcentury restored stone barn. We’re 15 minutes from Sight and Sound and the shops at Strasburg. With lots of trails and the Susquehanna River close by, your family can spend many hours hiking in southern Lancaster County. Experience the local Britain Hill Vineyard,coffee,and ice cream shops nearby. The charming city of Lancaster with its many authentic restaurants is only a 20 minute drive. We would love to have you come and enjoy the barn stay with us

A private swimming pool is surrounded by lounge chairs and landscaped greenery. The clear blue water reflects sunlight, and a white fence offers privacy. The pool area includes a concrete deck, creating an inviting space for relaxation and enjoyment.

4.91 out of 5 average rating, 106 reviews

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Apartment in Chesapeake City

A bright bedroom features a cozy bed adorned with a textured yellow coverlet and colorful accent pillows. Artwork and a bedside lamp are visible against the light walls. A vibrant area rug adds warmth, and a glimpse of the kitchen can be seen through an adjacent doorway.

4.94 out of 5 average rating, 105 reviews

hygge haven: hygge= happy + cozy

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

4.98 out of 5 average rating, 157 reviews

A spacious living area is shown, featuring a well-equipped kitchen, dining space for four, and a cozy seating area. Light green chairs provide a pop of color, while a large mirror reflects the room's dimensions. Soft natural light filters in from the window.

Guest suite in Newark

Charming Fully Equipped Private Guest Suite Studio

Relax in a stylish guest suite studio in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

4.98 out of 5 average rating, 594 reviews

A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.

Cottage in North East

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

4.95 out of 5 average rating, 198 reviews

An outdoor seating area features comfortable gray cushions and a dark wooden coffee table, positioned on a deck overlooking a serene waterfront. The vibrant sunset casts warm hues across the sky, reflecting on the calm water, creating a tranquil atmosphere.

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

4.99 out of 5 average rating, 128 reviews

A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.

Home in Perryville

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Place to stay in Airville

The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.

4.98 out of 5 average rating, 200 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

4.98 out of 5 average rating, 140 reviews

A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.

Guesthouse in Elk Mills

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

4.92 out of 5 average rating, 153 reviews

An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.

Guesthouse in Elkton

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

4.94 out of 5 average rating, 378 reviews

The cottage exterior features a white vinyl facade, framed by black shutters on the windows. A welcoming front porch with steps leads to a glass door, complemented by flowering plants in front, with a well-maintained lawn and clear evening lighting enhancing the inviting ambiance.

Cottage in North East

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Townhouse in Port Deposit

A bright and serene bedroom features a spacious bed with a light-colored quilt and decorative pillows. Two large windows offer natural light and views of lush greenery outside. A vintage dresser sits beside the bed, complemented by a nearby radiator.

4.96 out of 5 average rating, 227 reviews

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

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Popular amenities for Chesapeake City vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Chesapeake City

A spacious living area features a green sectional sofa arranged around a geometric wooden coffee table. Decorative items are displayed on a wall shelf, complemented by framed artwork. Soft lighting is provided by a lamp, creating a cozy atmosphere.

5 out of 5 average rating, 11 reviews

Captain’s Cottage Retreat

5 out of 5 average rating, 6 reviews

A welcoming porch is visible, framed by multiple windows allowing natural light to enter. The light yellow exterior contrasts with vibrant flower pots positioned along the steps. Scenic river views are seen in the background, enhancing the peaceful ambiance of the cottage.

Home in Earleville

Delightful 2BR River View Home!

Lounge chairs are positioned beside a private in-ground pool, accompanied by shaded umbrellas. Lush greenery enhances the outdoor space, while decorative planters add a touch of elegance along the poolside. A serene atmosphere invites relaxation in this inviting setting.

5 out of 5 average rating, 4 reviews

Historic Victorian Queen Chesapeake City

Superhost

A spacious living area showcases a large sectional sofa in earthy tones, paired with a rustic coffee table. The room features a chandelier and is illuminated by natural light from multiple windows, with an open connection to a modern kitchen and dining space in the background.

4.9 out of 5 average rating, 41 reviews

HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn

4.96 out of 5 average rating, 89 reviews

Two vibrant blue adirondack chairs are positioned beside a small, round table, creating an inviting outdoor seating area. In the background, the tranquil waters of the Bohemia River reflect the warm hues of sunset, framed by lush trees and marina boats.

Cottage in Earleville

The Bohemia Charmer

4.89 out of 5 average rating, 72 reviews

A tranquil waterfront scene captures the sun setting over calm waters, with vibrant orange and yellow hues reflecting off the surface. Lush greenery frames the image, offering a natural border that enhances the serene view.

Home in Elkton

Sunset River Cottage

5 out of 5 average rating, 6 reviews

Adirondack chairs are positioned on a grassy area overlooking the Chesapeake Bay. A small side table accompanies the chairs, providing a space for drinks or snacks. Trees provide shade to this serene outdoor spot, where the blue water and sky blend harmoniously.

Home in Earleville

Sweet Bay Overlook