House holiday rentals in Chesapeake City

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Top-rated house rentals in Chesapeake City

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite
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.
Home in Chesapeake City
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!

Guest favourite
The exterior of the home features a welcoming front porch with a black door and decorative shutters. An American flag hangs beside the entrance. A patio area is visible, furnished with a round table and chairs, surrounded by greenery and outdoor lighting.
Home in Elkton
4.83 out of 5 average rating, 387 reviews

Cozy Cottage Elkton North East 3bed 2 bath Patio

Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark& UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc. Relax, visit, enjoy each other NO TV's

Top guest favourite
A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator, microwave, and gas cooktop. An island with bar seating is positioned beside a spacious sink, while natural light streams through a window overlooking the exterior.
Home in Chesapeake City
5 out of 5 average rating, 100 reviews

Fall Season @ Old Lock View Chesapeake City MD

*We are Pet Friendly* Named for one of the original C&D Canal Locks, Old Lock View is a true breath of fresh air! Enjoy this recently renovated spacious older home with spacious rooms, plenty of off-street parking. Move from the indoor comfort to the outdoor entertaining patio with gazebo, BBQ grill, year-round outdoor firepits and patio table/chairs. Every detail has been thought of for your comfort. No parties Stay here when in town to attend family events like weddings and graduations etc.

Top guest favourite
A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.
Home in Chestertown
4.98 out of 5 average rating, 161 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Top guest favourite
A cozy bedroom features a spacious bed with a softly draped blanket. Decorative pillows add color, while muted teal and warm brown tones create a comfortable ambiance. A circular mirror and artwork complement the floral wallpaper, with ambient lighting provided by matching bedside lamps.
Home in Hockessin
4.97 out of 5 average rating, 539 reviews

Eclectic Escape Near Longwood Gardens & Mt. Cuba

Home information: Home owners are on the other side of house ( your space is very private). 1/2 the house is your space. Imagine a ranch house cut down the middle and 1/2 is the Airbnb and the other 1/2 is the owners side. Private entrance with keyless lock , 2 bedrooms with Queen beds, private bathroom and a living room. Other features include: Wifi , TV’s , a small refrigerator/freezer , microwave, coffee maker and a Private 1 acre lot w/ parking ( 2 cars max). There is no kitchen .

Guest favourite
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
4.97 out of 5 average rating, 144 reviews

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!

Top guest favourite
Aerial view of the waterfront property reveals expansive green lawns surrounded by lush trees, with the C&D Canal visible nearby. The water reflects the clear blue sky, and a boat is seen traversing the canal, highlighting the active water traffic and serene natural surroundings.
Home in Elkton
4.9 out of 5 average rating, 100 reviews

Waterfront Retreat for Weekends and More!

NEW: 1-Hour south of the Philadelphia World Cup Games!!! Games!!!Nature at its finest: Find peace and tranquility in this waterfront home with breathtaking water views from all freshly decorated rooms. Enjoy the water traffic on the C&D Canal along with the multitude of wildlife living in the area. Launch your kayak, canoe or row boat from the boat ramp. Relax here in the evenings while spending the day visiting the University of Delaware or other local Cecil County venues.

Guest favourite
A charming two-story red brick home features large windows with black shutters, allowing ample natural light to enter. Lush green landscaping surrounds the entrance, which includes a white front door flanked by elegant outdoor sconces. The overall impression reflects a well-maintained historic residence.
Home in North East
4.94 out of 5 average rating, 130 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.

Guest favourite
A spacious living area showcases a soft sofa, stylish armchair, and a wooden coffee table. A ceiling fan rotates gently above, while large windows allow natural light to illuminate the room. The dining area features a wooden table surrounded by six chairs, suited for gatherings.
Home in Newark
4.95 out of 5 average rating, 112 reviews

2 BR/1 BA/Office University of DE

Home of the fighting Blue Hens and the University of Delaware, Newark is centrally located to Philadelphia, Baltimore and surrounded by over 12,000 acres of beautiful parkland. Enjoy this recently renovated home with spacious rooms, a fully equipped kitchen and laundry and plenty of off-street parking. Every detail has been thought of for your comfort including free WIFI. Great for UD Events, Weddings, Anniversaries, Car Shows, Mountain Biking and Cycling Weekends, and more.

Top guest favourite
The exterior of the Tiny House is showcased, featuring a modern design with a gray metal facade. A welcoming entryway is installed with a wooden door. A brick walkway leads from the grass area to the entrance, framed by trees and landscaping, creating an inviting environment.
Home in Kennett Square
4.88 out of 5 average rating, 113 reviews

Newly built Tiny House in Historic Kennett Square

Custom-built tiny house Cottage with designer touches. Main floor has living area, full bath, and laundry. Loft bedroom with king bed and full ceiling height, accessed by stairs. Fully equipped kitchen with full appliances, cookware, table settings, and coffee. Smart TV, high-speed internet, and on-site parking. Two blocks from downtown Kennett Square dining, shops, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Max 2 guests.

Guest favourite
A welcoming entryway features a modern fireplace with a black brick surround, accompanied by a decorative 'welcome' sign above. Light wood flooring extends into the space, leading toward doorways that open into additional rooms.
Home in Newark
4.85 out of 5 average rating, 176 reviews

Modern 3 bedroom ranch house/5 min from UD

Discover the perfect blend of comfort and convenience at this modern ranch style home in the heart of Newark. Just minutes from the University of Delaware and the scenic Newark Reservoir, this fully updated space is ideal for families, friends, or visiting professionals looking to relax in comfort while staying close to it all.

Guest favourite
A spacious living area features a corner sectional couch adorned with light blue and white pillows. Natural light filters through two windows, illuminating a wooden coffee table positioned in front of the couch. Framed artwork is displayed on the walls.
Home in Port Deposit
4.9 out of 5 average rating, 143 reviews

Quarry Landing * River View & Pet Friendly

Charming 3 bedroom duplex in Historic Port Deposit, MD. Enjoy vintage style with modern comfort: memory foam beds, full kitchen, laundry, Wi-Fi. Walk to waterfront, dining, playground, dog park & more. Safe, quiet neighborhood—perfect for couples, families, or a peaceful getaway. Book now and enjoy a stay by the river!

Popular amenities for house rentals in Chesapeake City

Quick stats about house rentals in Chesapeake City

  • Total holiday rentals

    Explore 10 holiday rentals in Chesapeake City

  • Nightly prices starting at

    Chesapeake City holiday rentals start at $267 SGD per night before taxes and fees

  • Verified guest reviews

    Over 710 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Chesapeake City holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake City rentals

  • 5 Average rating

    Chesapeake City stays are highly rated by guests – averaging 5 out of 5!

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