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Vacation rentals in Chesapeake City

Vacation rentals in Chesapeake City

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesapeake City

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Summer Wedding, Winery season Chesapeake City MD
    SUPERHOSTEntire house · 8 guests · 3 beds · 2.5 bathrooms
    Summer Wedding, Winery season Chesapeake City MD

    Named for one of the original Chesapeake & Delaware 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. UD Graduation (20 Min. drive) , Weddings, Anniversary's, Car Show, Biking Weekend, Girls weekend

    What guests are saying:

    “Fred & Toni's hospitality and attention to traveling details are top rate. They thought out every possible need we had. Towels, chocolates & face wipes were placed in every room for our 4 girl's weekend. The home was super clean and inviting. All of my girlfriends are so excited to book another excursion in the late spring with Fred & Toni. This home comes highly recommended for Girl's & Family Vacations, also a sweet for Honeymooners Delight. Walking distance from the canal with magnificent sunsets and picturesque photo ops. Very quiet and serene. Kimberly”

  • Cafe on the Bay 2
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 shared bathroom
    Cafe on the Bay 2

    We are in the heart of historic Chesapeake City on the C&D canal. Tourists enjoy antique shopping and cute little shops with top notch dining options all within walking distance. We are a block away from the 3 wedding venues in town. We have 2 bedrooms above the cafe with queen beds and a full bathroom in the hallway for guests. This is a great location for 2 couples or a family as it is a shared bathroom for the 2 rooms.

    What guests are saying:

    “The Cafe by the Bay is a great spot right in the middle of town. We had a blast visiting Chesapeake City. Tammy and her staff made everything easy.”

  • Cozy Stay Near University of Delaware
    SUPERHOSTPrivate room · 6 guests · 3 beds · 1.5 bathrooms
    Cozy Stay Near University of Delaware

    Our house is centrally located in a quiet neighborhood in Northern Delaware. Our house is 5 miles off of I-95, with close proximity to both Baltimore & Philadelphia. Our home is the perfect destination for couples traveling through the Mid-Atlantic or visiting their university student. While our home has 3 separate guest bedrooms, we only host one booked group at a time. We are a short drive from the C&D Canal with beautiful sites and restaurants. Our driveway is available for parking.

    What guests are saying:

    “Ron and Anne's place is in a nice, quiet, and safe residential neighborhood. It's located about a 20 minute drive from Chesapeake City's main street area, where we were attending a wedding reception. It was a great location for us with the sunroom and outdoor deck to lounge and mingle. Their home is lovely and clean with all the amenities you would need for a great and comfortable stay while traveling. They are both very friendly hosts that makes one feel welcomed upon arrival and lucky to be guests in their home.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesapeake City holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chesapeake City

Persimmon Pastures
SUPERHOSTEntire cottage
Persimmon Pastures
Price:€72 / night
The people's house.
SUPERHOSTPrivate room
The people's house.
Price:€35 / night
The Gray Room & Additional Guest Areas
SUPERHOSTPrivate room
The Gray Room & Additional Guest Areas
Price:€35 / night
High-End Cottage, Water View, Chesapeake City, MD
SUPERHOSTEntire guest house
High-End Cottage, Water View, Chesapeake City, MD
Price:€155 / night
Private room and bath in second floor.
SUPERHOSTPrivate room
Private room and bath in second floor.
Price:€44 / night
Cozy King Bedroom near Christiana Hospital & Mall
SUPERHOSTPrivate room
Cozy King Bedroom near Christiana Hospital & Mall
Price:€28 / night
Waterfront Cabin on the Chesapeake
SUPERHOSTEntire cabin
Waterfront Cabin on the Chesapeake
Price:€310 / night
Chesapeake City MD Staycation
Entire house
Chesapeake City MD Staycation
Price:€265 / night
Broken Spoke Winery Cottage
SUPERHOSTFarm stay
Broken Spoke Winery Cottage
Price:€166 / night
Private home
SUPERHOSTEntire house
Private home
Price:€66 / night
Carriage House Suite on NE Creek!
SUPERHOSTPrivate room
Carriage House Suite on NE Creek!
Price:€97 / night
Appleton Retreat
SUPERHOSTEntire house
Appleton Retreat
Price:€111 / night
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