Holiday houses in Chesapeake City

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Top-rated holiday rentals in Chesapeake City

Guests agree: these stays 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
Apartment in Chesapeake City
4.94 out of 5 average rating, 111 reviews

Hygge Haven: A cozy apartment in a canal-side town

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.

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 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
4.98 out of 5 average rating, 645 reviews

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.

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!

Guest favourite
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
4.91 out of 5 average rating, 174 reviews

Countryside-Stablehouse-Open Studio-Perfect 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

Top Guest favourite
Cottage in Charlestown
4.95 out of 5 average rating, 244 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a WINTRY romantic couple's getaway! honeymoon/celebrations Designed with that in mind,a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & 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

Top Guest favourite
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
4.95 out of 5 average rating, 404 reviews

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.

Guest favourite
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.
Townhouse in Port Deposit
4.95 out of 5 average rating, 239 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.

Top Guest favourite
A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.
Cottage in Chesapeake City
5 out of 5 average rating, 107 reviews

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

Top Guest favourite
A light green wall complements a cozy sleeping area, featuring a spacious bed adorned with a textured beige quilt and a decorative pillow. A bedside table with a stylish lamp provides soft lighting, while a window allows natural light and greenery to fill the space.
Apartment in New Castle
4.9 out of 5 average rating, 201 reviews

Green Sanctuary-Pvt Apt for Quiet Rest

Green Sanctuary is the second floor apartment B in a two unit apartment building. It is a bright cheerful one bedroom unit with a large covered balcony located on the grounds of the famous Egyptian house. The apartment is comfortable for 2 people but will accommodate 4 with the living room couch converting to a bed. The property is conveniently located with plenty of off street parking.

Top Guest favourite
A charming cottage is nestled among lush greenery, with a large window inviting natural light. The exterior features a sloping roof and a stone wall, accentuating the surrounding landscape of rolling hills and fields.
Cottage in Coatesville
5 out of 5 average rating, 324 reviews

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.

Popular amenities for Chesapeake City holiday rentals

When is the best time to visit Chesapeake City?

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Avg. price$452 NZD$343 NZD$328 NZD$313 NZD$348 NZD$346 NZD$358 NZD$355 NZD$468 NZD$366 NZD$368 NZD$351 NZD
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Chesapeake City?

    Yes! Work meets play with ease at over 10 vacation rentals in Chesapeake City featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Chesapeake City?

    Experience the best of Chesapeake City with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chesapeake City have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Chesapeake City. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Chesapeake City?

    Chesapeake City has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Chesapeake City

  • Total holiday rentals

    Explore 30 holiday rentals in Chesapeake City

  • Nightly prices starting at

    Chesapeake City holiday rentals start at $134 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chesapeake City holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Chesapeake City rentals

  • 5 Average rating

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

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