
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$39,769 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!
LocationValueOutdoor spaces
4.9 out of 5 average rating, 118 reviews
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
FamilyValueBeach
4.82 out of 5 average rating, 404 reviews
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.
FamilyLocationTV
5.0 out of 5 average rating, 104 reviews
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.
LocationFamilyLaundry
4.98 out of 5 average rating, 197 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!
ValueLocationBeach
4.96 out of 5 average rating, 171 reviews
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.
ValueFamilyPool
4.96 out of 5 average rating, 137 reviews
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.
LocationFamilyLaundry
4.94 out of 5 average rating, 142 reviews
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.
ValueLocationLaundry
4.96 out of 5 average rating, 170 reviews
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!
LocationFamilyLayout
4.96 out of 5 average rating, 105 reviews
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.
FamilyLocationCheckout
4.92 out of 5 average rating, 249 reviews
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.
ValueLocationWifi
4.96 out of 5 average rating, 107 reviews
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
LocationValueOutdoor spaces
4.91 out of 5 average rating, 119 reviewsPopular amenities for Chesapeake City house rentals
House rentals with a pool

Secluded Home | Year Round heated Pool & Waterfall
ValueLocationNearby
4.96 out of 5 average rating, 137 reviews
Historic Victorian Walkability Chesapeake City
FamilyLocationPool
5.0 out of 5 average rating, 15 reviews
Veazey Cove Lodge Wellness Retreat /Sauna/ Hot Tub
FamilyLocationBeach
4.93 out of 5 average rating, 42 reviews
Breathtaking Waterfront - Christmas on the Water!
LocationFamilyHot tub
4.95 out of 5 average rating, 20 reviews
The Hidden Gem•Heated pool•Pickleball Court
LocationFamilyPets
4.99 out of 5 average rating, 90 reviews
Cording Lodge*Pool*Pickleball/Basketball court
FamilyLocationAccess
4.94 out of 5 average rating, 32 reviews
Waterfront Wellness - *With Sauna and Hot Tub!*
LocationFamilyIndoor spaces
4.91 out of 5 average rating, 32 reviews
Spacious family home w/pool, sauna & hot tub
FamilyLocationSleep quality
5.0 out of 5 average rating, 24 reviewsWeekly house rentals

Entire home walking distance from downtown
LocationFamilyGrill
4.99 out of 5 average rating, 110 reviews
“Home Away from Home” in Rising Sun, Maryland
LocationFamilyAccess
4.96 out of 5 average rating, 337 reviews
High Tide & Hound
ValueLocationCondition
4.97 out of 5 average rating, 102 reviews
The Garden Estate: Historic Town Center Home
ValueFamilyBackyard
5.0 out of 5 average rating, 253 reviews
Chesapeake City Charm at the Boho House!
FamilyLocationSleep quality
5.0 out of 5 average rating, 66 reviews
McReynolds-Woods House -Private 3 Bedroom Home
FamilyLocationAccuracy
5.0 out of 5 average rating, 67 reviews
Canal views/Walk to Shops/Luxury 2Bed/1.5Bath
FamilyValueIndoor spaces
5.0 out of 5 average rating, 32 reviews
Modish Cottage - Walk to everything!
LocationValueNearby
5.0 out of 5 average rating, 31 reviewsPrivate house rentals

Stunning 2BR Cottage w/River views
LocationFamilyComfort
4.96 out of 5 average rating, 23 reviews
The River House - waterfront
LocationValueAir conditioning
4.97 out of 5 average rating, 35 reviews
Wister Loft: Charm & History with Modern Love.
LocationConditionAccuracy
5.0 out of 5 average rating, 46 reviews
Sweet Bay Overlook
ValueFamilyCondition
5.0 out of 5 average rating, 52 reviews
Waterfront House on the Upper Chesapeake Bay
ValueFamilyOutdoor spaces
4.84 out of 5 average rating, 50 reviews
The Cottage at Crystal
LocationIndoor spacesWifi
4.95 out of 5 average rating, 38 reviews
Riverfront Haven @ Hances Point
LocationFamilyKitchen
5.0 out of 5 average rating, 33 reviews
The Sunset House-Hot Tub-Sauna
LocationFamilyKitchen
4.95 out of 5 average rating, 91 reviewsDestinations to explore
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