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Vacation rentals in Chesapeake City

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesapeake City

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

The Mint Cottage in Chesapeake City
Entire residential home · 6 guests · 4 beds · 3 baths

The Mint Cottage in Chesapeake CityThe 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!

Benson House on Bohemia Ave (Back Deck)
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath

Benson House on Bohemia Ave (Back Deck)Private entrance to your own “hotel room” within walking distance to all of the hot spots in town. Room includes private bath, microwave, small refrigerator and private deck for enjoying your morning coffee or tea. Downstairs is a small fire pit and Adirondack chairs for use.

Chesapeake Charm in Historic Chesapeake City, MD
Entire rental unit · 4 guests · 1 bed · 1 bath

Chesapeake Charm in Historic Chesapeake City, MDCharming One bedroom apartment in historic Chesapeake City, MD. Located within walking distance to local restaurants and nightlife. You will enjoy shopping in the heart of town at the local boutiques and shops. Nearby walking and biking trails are perfect for the adventurous tourist! The canal and bridge create a picture-perfect background for anyone! If you are lucky enough to see a ship pass through during your stay be sure to snap a picture it’s a fascinating sight!

Vacation rentals for every style

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Popular amenities for Chesapeake City vacation rentals

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

Other great vacation rentals in Chesapeake City

SUPERHOST
  1. Entire cottage
  2. North East
Bittersweet Cottage
  1. Entire cottage
  2. North East
Cottage by the Chesapeake
SUPERHOST
  1. Private room
  2. Chesapeake City
Cafe on the Bay 2- breakfast included!
SUPERHOST
  1. Entire guest suite
  2. North East
The Cozy Studio of North East MD
SUPERHOST
  1. Entire cottage
  2. North East
Cottage Just Off North East's Main Street
SUPERHOST
  1. Private room
  2. Chesapeake City
Benson House on Bohemia Ave. - Front
  1. Entire residential home
  2. Elkton
Elkton North East 3bed 2 bath Family Patio wi-fi
SUPERHOST
  1. Entire residential home
  2. Chesapeake City
Summer Wedding, Winery season Chesapeake City MD
SUPERHOST
  1. Entire guesthouse
  2. Chesapeake City
High-End Cottage, Water View, Chesapeake City, MD
SUPERHOST
  1. Entire rental unit
  2. Chesapeake City
Chesapeake City Great House Farm apartment
SUPERHOST
  1. Entire rental unit
  2. Chesapeake City
The Checkered Rabbit
SUPERHOST
  1. Entire residential home
  2. Elkton
Serene Hideaway

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