
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

A Waterfront Christmas for 2025 is still available

Historic Victorian Queen Chesapeake City

The Mint Cottage in Chesapeake City

Pool House by the North East River

Cording Lodge*Pool*Pickleball/Basketball court

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

Chesapeake Waterfront Retreat W/Pool.
Weekly house rentals

Riverfront Haven @ Hances Point

Connection Pointe•River views•Quiet•Peaceful

Water View Historic B & B - Gift Card Included

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

Sunset River Cottage

Waterfront House on the Upper Chesapeake Bay

Newly built Tiny House in Historic Kennett Square

Wister Loft: Charm & History with Modern Love.
Private house rentals

Grandma’s Cottage

Waterfront Paradise w/ Pier - kayak to Chestertown

Chesapeake Waterfront Vacation Rental with Dock

Lark's Nest on the Chester River

Catching Sunsets on the Bay

The Cooper House in Charlestown, MD

Boho River Cottage

Ruby's Sea Glass Cottage near Betterton Beach
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
R2,778 ZAR before taxes and fees
Total number of reviews
650 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
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Outer Banks Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- M&T Bank Stadium
- Fortescue Beach
- Longwood Gardens
- Fairmount Park
- Oriole Park at Camden Yards
- Betterton Beach
- Penn's Landing
- Hampden
- Philadelphia Museum of Art
- Sandy Point State Park
- 30th Street Station
- French Creek State Park
- Marsh Creek State Park
- Philadelphia Zoo
- Aronimink Golf Club
- The Franklin Institute
- Big Stone Beach
- Wells Fargo Center
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Valley Forge National Historical Park