
House vacation rentals in Chesapeake City
Find and book unique houses on Airbnb
Quick stats about house rentals in Chesapeake City

Total vacation rentals
Explore 10 vacation rentals in Chesapeake City

Nightly prices starting at
Chesapeake City vacation rentals start at G$39,667 GYD per night before taxes and fees

Verified guest reviews
Over 780 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chesapeake City vacation rentals include wi-fi 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!
LocationValueAir conditioning

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
FamilyValueEV charging

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.
ValueFamilyCheck-in

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.
LocationValuePets

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!
LocationValueGetting around

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.
LocationValueCondition

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.
FamilyValueGetting around

River front cottage with private dock & water fun
Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!
ValueFamilyCheck-in

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.
FamilyLocationWalkability

Waterfront Retreat w/ Hot Tub, Games & Views
Escape to River Haven, a 7,000+ sq. ft. waterfront retreat on the Susquehanna River, perfect for groups of up to 20. Relax in the hot tub, play pickleball, pool, ping-pong, and air hockey, or unwind on expansive decks with scenic views. The home features a fully equipped kitchen, spacious bedrooms, 4.5 baths, and family-friendly amenities. With a kayak launch nearby, trailer parking, and a whole-house generator, River Haven is made for memorable getaways.
ValueLocationKitchen

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
ValueLocationWifi

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.
ValueLocationLayout
Popular amenities for Chesapeake City house rentals
House rentals with a pool

Secluded Home | Year Round heated Pool & Waterfall
FamilyValueGetting around

Historic Victorian Walkability Chesapeake City
LocationFamilyOutdoor spaces

Breathtaking Waterfront w/pool and private dock
LocationFamilyNearby

River Heights Retreat Heated pool and hot tub)
FamilyValueSleep quality

The Hidden Gem•Heated pool•Pickleball Court
FamilyValueSleep quality

Cording Lodge*Pool*Pickleball/Basketball court
FamilyLocationCheck-in

Spacious family home w/pool, sauna & hot tub
FamilyLocationPool

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

Historic Creekside Home - 2br 2.5ba Downtown
LocationFamilyBathroom

“Home Away from Home” in Rising Sun, Maryland
LocationValueLong stay

The Garden Estate: Historic Town Center Home
FamilyLocationComfort

Classic Victorian in Chestertown
ValueLocationSleep quality

Modern 3 bedroom ranch house/5 min from UD
LocationValueParking

High Tide & Hound
LocationValueWifi

Chesapeake City Charm at the Boho House!
FamilyLocationKitchen

McReynolds-Woods House -Private 3 Bedroom Home
LocationFamilyCleanliness
Private house rentals

Charming, updated home in Historic Chesapeake City
FamilyLocationKitchen

Stunning 2BR Cottage w/River views
FamilyLocationAmenities

Connection Pointe•River views•Quiet•Peaceful
ValueLocationComfort

The Cottage at Crystal
LocationCleanlinessAccess

Wister Loft: Charm & History with Modern Love.
LocationOutdoor spacesCleanliness

The River House - waterfront
ValueFamilyDecor

Waterfront House on the Upper Chesapeake Bay
FamilyLocationAccess

Sweet Bay Overlook
FamilyValueBeach
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- M&T Bank Stadium
- Pennsylvania Convention Center
- Longwood Gardens
- Wells Fargo Center
- University of Pennsylvania
- Citizens Bank Park
- Fairmount Park
- Johns Hopkins University
- Federal Hill Park
- Oriole Park at Camden Yards
- Philadelphia Museum of Art
- Dutch Wonderland
- Temple University
- Betterton Beach
- CFG Bank Arena
- Baltimore Convention Center
- Dover Motor Speedway
- Amish Village
- University of Delaware
- Drexel University
- French Creek State Park
- Lincoln Financial Field
- Philadelphia Zoo
- Patterson Park





