
House vacation 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.
Vacation 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

Findley Farm View Cottage (Outdoor Pool!)

Amazing pool and Hot Tub!

Beautiful Home Near Beach and Patapsco River

Breathtaking Waterfront Now booking Fall 2025

Modern Farmhouse: Pool, Hot Tub & Pickleball

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

Yellow Door Cottage

Lark's Nest on the Chester River

Spacious 3Bed/2Bath near UD / Christiana Hospital

Waterfront Paradise on the Bay

Catching Sunsets on the Bay

Water View Historic B & B - Gift Card Included

HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn

The Cooper House in Charlestown, MD
Private house rentals

Rogue Wave River Retreat

-Scenic Historic Charm- Spruce Edge Guest House

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Quaint home in charming town

Waterfront Family Vacation Home

Ruby's Sea Glass Cottage near Betterton Beach

Cheerful and Cozy Charming Home

The Fishing Factory
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
R2,871 ZAR 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
Wifi availability
10 properties include access to wifi
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- Pennsylvania Convention Center
- Lincoln Financial Field
- Fortescue Beach
- Citizens Bank Park
- Betterton Beach
- Fairmount Park
- Penn's Landing
- Longwood Gardens
- Oriole Park at Camden Yards
- Wells Fargo Center
- Dutch Wonderland
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Philadelphia Museum of Art
- The Franklin Institute
- Philadelphia Zoo
- Patterson Park
- 30th Street Station
- Aronimink Golf Club
- French Creek State Park
- Marsh Creek State Park
- Wissahickon Valley Park
- Independence Hall