
House holiday rentals in Chesapeake City
Find and book unique houses on Airbnb
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 $259 SGD per night before taxes and fees

Verified guest reviews
Over 720 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!
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!

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

Summer 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.

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.

Harbor View Haven | Waterfront w/ Hot Tub + Dock!
BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

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!

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.

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.

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.

Beautiful Large Home in Private Woods with Hot Tub
Welcome to Elk Creek Lodge, an expansive and secluded sanctuary nestled on 18 acres of lush woods and meadows. Situated just a short drive from historic Oxford, Pennsylvania. Also conveniently located to horse riding events in Fair Hill, MD. Scan the QR code for a virtual tour. Distance from Attractions: Fairwinds Farm - 6.8 mi Fair Hill Training Center & Fair Hill International - 7.6 mi Great Wolf Lodge Water Park - 17.4 mi
Popular amenities for house rentals in Chesapeake City
House rentals with a pool

Secluded home pool & waterfall - Amish community

Breathtaking Waterfront w/pool and private dock

Historic Victorian Queen Chesapeake City

Cording Lodge*Pool*Pickleball/Basketball court

The Hidden Gem•Heated pool•Pickleball Court

Good Times and Tan Lines | Poolhouse Dover Escape

Spacious family home w/pool, sauna & hot tub

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

River front cottage with private dock & water fun

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

Canal views/Walk to Shops/Luxury 2Bed/1.5Bath

Sweet Bay Overlook

Charming, updated home in Historic Chesapeake City

Breathtaking views!

Chesapeake City MD Staycation

“Home Away from Home” in Rising Sun, Maryland
Private house rentals

Riverfront Haven @ Hances Point

The River House - waterfront

Chesapeake Waterfront Vacation Rental with Dock

Connection Pointe•River views•Quiet•Peaceful

Stunning 2BR Cottage w/River views

Catching Sunsets on the Bay

Chesapeake Bay Retreat W/Breathtaking Views

Waterfront House on the Upper Chesapeake Bay
Destinations to explore
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- M&T Bank Stadium
- Pennsylvania Convention Center
- Longwood Gardens
- Citizens Bank Park
- Wells Fargo Center
- Fairmount Park
- Baltimore Convention Center
- University of Pennsylvania
- Oriole Park at Camden Yards
- Federal Hill Park
- Johns Hopkins University
- Philadelphia Museum of Art
- Dutch Wonderland
- Betterton Beach
- CFG Bank Arena
- Dover Motor Speedway
- Philadelphia Zoo
- Temple University
- University of Delaware
- French Creek State Park
- Patterson Park
- Drexel University
- 30th Street Station
- Marsh Creek State Park





