
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.

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

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.

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.

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

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!

Countryside-Stable House-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

Conowingo Creek Casual
Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm, with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

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.

Waterfront Retreat for Weekends and More!
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.

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.

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.

The River Cottage
Take it easy in this unique cottage built in the 1800s nestled upon the Granite Cliffs of Port Deposit Maryland. While enjoying your tranquil get away you’re minutes from local shops, local dining, local wineries, local breweries and a local marina. There is plenty of sightseeing and wildlife. If you enjoy fishing and kayaking it’s just a short distance away.
Popular amenities for Chesapeake City holiday rentals
Other great holiday rentals in Chesapeake City

“Out to Sea” at the Terry House !

Captain’s Cottage Retreat

Historic Victorian Queen Chesapeake City

Cafe on the Bay 2- breakfast included!

Gardency House Room 1

Historic Chesapeake City Stay

Breathtaking views!

Delightful 12x16 Glamping Gazebo/Tent
When is the best time to visit Chesapeake City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $478 NZD | $363 NZD | $347 NZD | $331 NZD | $369 NZD | $367 NZD | $379 NZD | $376 NZD | $496 NZD | $399 NZD | $349 NZD | $374 NZD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 25°C | 24°C | 21°C | 14°C | 8°C | 3°C |
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 $177 NZD per night before taxes and fees

Verified guest reviews
Over 1,790 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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