
House holiday rentals in Chesapeake City
Find and book unique houses on Airbnb
Top-rated house rentals in Chesapeake City
Guests agree: these houses are highly rated for location, cleanliness and more.

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!

Spring 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.

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!

Home Away from Home in Rising Sun, MD
PLEASE READ *BEDROOM 3 is a suite that can be added for an extra charge (see pics) * It includes a living area, king size bed, bathroom and kitchenette. Ask Karen for pricing to add. Without the suite there is a foyer leading to a large living room, kitchen with dining area, 2 bedrooms with queen beds and a full bath. This home is comfy and has a history room showing family collectibles dating back to 1854.... Children under 12 years of age are not suitable and No Pets are allowed.

Red Point Lighthouse
Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

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.

Gunpowder Retreat
Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Waterfront Retreat for Weekends and More!
NEW: 1-Hour south of the Philadelphia World Cup Games (FIFA)!!! 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.

Appleton Retreat
This 3 bedroom, 2 bathroom home is the perfect place to get away from it all while remaining convenient to all the best that Maryland, Delaware, and Pennsylvania have to offer. Minutes from Fair Hill Natural Resource Management Area for the horseback riders, mountain bikers, hikers and nature enthusiasts. University of Delaware is a quick 10 minute ride away to catch a football game or celebrate commencement. Other local attractions - boating, fishing, vineyards and breweries.

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 of the Chesapeake - Private Waterfront Home
Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Creek home with pool & waterfall heated all year
Welcome to Quiet Brook Oasis Treat yourself to a relaxing weekend in this beautiful secluded creekfront home nestled in the woods that has a private inground pool, with a waterfall opened and heated all year. Located in peaceful Amish country, southern Lancaster county this newly remodeled home is sure to offer a relaxing and peaceful getaway. This is a perfect retreat for family or a couples romantic weekend. Find us on social media!
Popular amenities for house rentals in Chesapeake City
House rentals with a pool

Breathtaking Waterfront w/pool and private dock

Modern Farmhouse: Pool, Hot Tub & Pickleball

Cording Lodge*Pool*Pickleball/Basketball court

Sweet home w/pool & woods at peaceful Glen Mills

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

Lux Family Retreat l Sauna+Hot Tub *Games~Swingset

The Peaceful Getaway (with private pool & hot tub)
Weekly house rentals

Grandma’s Cottage

Riverfront Haven @ Hances Point

Chesapeake Waterfront Vacation Rental with Dock

Connection Pointe•River views•Quiet•Peaceful

Waterfront Paradise on the Bay

Catching Sunsets on the Bay

Stunning Chesapeake Bay views, 5 bedrooms, 3 bath

Sunset River Cottage
Private house rentals

The Sunset House-Hot Tub-Sauna

Casa Domino: A Peaceful Waterfront Retreat

Countryside Cottage

Water View Historic Tennis Club - 3br 2.5bath

Chesapeake Bay Retreat W/Breathtaking Views

Ruby's Sea Glass Cottage near Betterton Beach

Baybreeze Cottage

The Keithley House
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 £159 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!
Destinations to explore
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- Pennsylvania Convention Center
- Lincoln Financial Field
- M&T Bank Stadium
- Citizens Bank Park
- Longwood Gardens
- Fairmount Park
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Wells Fargo Center
- Philadelphia Museum of Art
- Penn's Landing
- Temple University
- Dutch Wonderland
- Sandy Point State Park
- Betterton Beach
- University of Pennsylvania
- Philadelphia Zoo
- Patterson Park
- 30th Street Station
- The Franklin Institute
- French Creek State Park
- Marsh Creek State Park
- Valley Forge National Historical Park
- Wissahickon Valley Park




