
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!

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

Fall 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.

Eclectic Escape Near Longwood Gardens & Mt. Cuba
Home information: Home owners are on the other side of house ( your space is very private). 1/2 the house is your space. Imagine a ranch house cut down the middle and 1/2 is the Airbnb and the other 1/2 is the owners side. Private entrance with keyless lock , 2 bedrooms with Queen beds, private bathroom and a living room. Other features include: Wifi , TV’s , a small refrigerator/freezer , microwave, coffee maker and a Private 1 acre lot w/ parking ( 2 cars max). There is no kitchen .

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!

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

Tranquil Carriage House*MCM *Country *Wildlife
The Aberdeen Carriage House is in a country setting with a country road. We are near city limits and have most of your needs right here. You have a grocery store, dollar store, Target, Walgreens, Planet Fitness, and restaurants in five minutes. Historic Havre de Grace, Ripken Stadium, Vineyards, Boating, and Golfing, only ten minutes. Baltimore and Stadiums are only 35 minutes down I95. The house is spotless and fully loaded with all the comforts of home—pet and chemical-free space.

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.

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.

Newly built Tiny House in Historic Kennett Square
Custom-built tiny house Cottage with designer touches. Main floor has living area, full bath, and laundry. Loft bedroom with king bed and full ceiling height, accessed by stairs. Fully equipped kitchen with full appliances, cookware, table settings, and coffee. Smart TV, high-speed internet, and on-site parking. Two blocks from downtown Kennett Square dining, shops, and breweries. Near Longwood Gardens and Brandywine Valley attractions. Max 2 guests.

Modern 3 bedroom ranch house/5 min from UD
Discover the perfect blend of comfort and convenience at this modern ranch style home in the heart of Newark. Just minutes from the University of Delaware and the scenic Newark Reservoir, this fully updated space is ideal for families, friends, or visiting professionals looking to relax in comfort while staying close to it all.
Popular amenities for Chesapeake City house rentals
House rentals with a pool

Cozy home- heated pool & waterfall heated all year

Breathtaking Waterfront w/pool and private dock

Modern Farmhouse: Pool, Hot Tub & Pickleball

Cording Lodge*Pool*Pickleball/Basketball court

Coastal Escape, in The Heart of Rock Hall!

Sweet home w/pool & woods at peaceful Glen Mills

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.
Weekly house rentals

Private Guest Suite

The Lighthouse

The River House - waterfront

Casa Domino: A Peaceful Waterfront Retreat

Connection Pointe•River views•Quiet•Peaceful

Catching Sunsets on the Bay

Wister Loft: Charm & History with Modern Love.

The Cottage at Crystal
Private house rentals

Grandma’s Cottage

Modern house in the country

Charming 3-Bed Single Level Cottage

Historic Cottage | 1min DT | Views | W/D | Parking

Spacious, Quiet & Peaceful

Two bedroom small ranch with beautiful forest view

Spacious 3BR/2BA near UD/Christiana Care Hospital

High Tide & Hound
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 $302 AUD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Chesapeake City holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Longwood Gardens
- Citizens Bank Park
- Fairmount Park
- Baltimore Convention Center
- Oriole Park at Camden Yards
- Philadelphia Museum of Art
- Penn's Landing
- Hampden
- Wells Fargo Center
- Betterton Beach
- Sandy Point State Park
- French Creek State Park
- Patterson Park
- Philadelphia Zoo
- The Franklin Institute
- Marsh Creek State Park
- Wissahickon Valley Park
- Valley Forge National Historical Park
- Independence Hall
- Eastern State Penitentiary
- Franklin Square




