
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 $323 NZD per night before taxes and fees

Verified guest reviews
Over 780 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, 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!
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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
FamilyValueParks

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.
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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.
FamilyLocationQuiet

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
LocationFamilyQuiet

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!
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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.
LocationFamilyDecor

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.
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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.
ValueFamilyCheckout

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.
ValueFamilyNearby

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.
LocationFamilyHospitality

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

Secluded home pool & waterfall - Amish community
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Historic Victorian Walkability Chesapeake City
LocationFamilyParks

Breathtaking Waterfront w/pool and private dock
LocationFamilyPets

Waterfront Wellness - *With Pool and Hot Tub!*
LocationFamilyAmenities

Peaceful Pines Hideaway
LocationFamilyNearby

Cording Lodge*Pool*Pickleball/Basketball court
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The Hidden Gem•Heated pool•Pickleball Court
LocationFamilySleep quality

River Heights Retreat (hot tub and luxury)
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Weekly house rentals

White Clay Creek Cottage
LocationFamilyBathroom

“Home Away from Home” in Rising Sun, Maryland
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The Fishing Factory
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Canal views/Walk to Shops/Luxury 2Bed/1.5Bath
FamilyLocationWalkability

McReynolds-Woods House -Private 3 Bedroom Home
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Modish Cottage - Walk to everything!
ValueFamilyAccuracy

Chesapeake City Charm at the Boho House!
FamilyLocationNearby

Breathtaking views!
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Private house rentals

Sweet Bay Overlook
ValueFamilyIndoor spaces

Waterfront House on the Upper Chesapeake Bay
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Chesapeake City MD Staycation
ValueLocationBeach

Riverfront Haven @ Hances Point
LocationFamilyHospitality

Connection Pointe•River views•Quiet•Peaceful
LocationFamilyBathroom

The River House - waterfront
LocationValueAmenities

Elegant Spacious Family Gem • 20 Min to Wilmington
LocationAmenitiesIndoor spaces

Ruby's Sea Glass Cottage near Betterton Beach
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Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Virginia Beach Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Newark Holiday rentals
- Richmond Holiday rentals
- Outer Banks Holiday rentals
- M&T Bank Stadium
- Pennsylvania Convention Center
- Longwood Gardens
- Baltimore Convention Center
- Wells Fargo Center
- Citizens Bank Park
- University of Pennsylvania
- Fairmount Park
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Philadelphia Museum of Art
- Dutch Wonderland
- CFG Bank Arena
- Betterton Beach
- Temple University
- University of Delaware
- Drexel University
- Amish Village
- Dover Motor Speedway
- French Creek State Park
- Philadelphia Zoo
- 30th Street Station
- Marsh Creek State Park





