
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake City house rentals
House rentals with a pool

Chestertown Watson Family Farm

Private Pool, Botanical Hot Tub, Fire Garden

Breathtaking Waterfront Now booking Fall 2025

Sweet home w/pool & woods at peaceful Glen Mills

Gunpowder Retreat

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

Waterfront Poolside Escape
Weekly house rentals

Yellow Door Cottage

The River House - waterfront

Weekday Special | Newly Built | Designer House

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

Water View Historic B & B - Gift Card Included

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

The Cooper House in Charlestown, MD

Sunset River Cottage
Private house rentals

Lark's Nest on the Chester River

Catching Sunsets on the Bay

Waterfront Family Vacation Home

Beautiful Large Home in Private Woods with Hot Tub

The Fishing Factory

Lotus House: porches, decks, yard, beach access

Farm House w/ Water Access (near Chestertown)

The Keithley House
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
$270 NZD before taxes and fees
Total number of reviews
570 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 properties include access to Wi-Fi
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Outer Banks Holiday rentals
- South Jersey Holiday rentals
- The Hamptons Holiday rentals
- Mount Pocono Holiday rentals
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Fairmount Park
- Oriole Park at Camden Yards
- Dutch Wonderland
- Longwood Gardens
- Penn's Landing
- Wells Fargo Center
- M&T Bank Stadium
- Sandy Point State Park
- Philadelphia Museum of Art
- Hampden
- The Franklin Institute
- Patterson Park
- Aronimink Golf Club
- Philadelphia Zoo
- 30th Street Station
- Marsh Creek State Park
- French Creek State Park
- Crystal Beach Manor, Earleville, MD
- Wissahickon Valley Park
- Franklin Square
- Independence Hall