
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 house rentals in Chesapeake City
House rentals with a pool

Chestertown Watson Family Farm

Spend Fall Days in Nature Wedding Season

A Waterfront Christmas for 2025 is still available

Rockfish Keeper

The Mariner's House

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

The Peaceful Getaway (with private pool & hot tub)
Weekly house rentals

Waterfront Retreat for Weekends and More!

Lark's Nest on the Chester River

Connection Pointe•River views•Quiet•Peaceful

Water View Historic B & B - Gift Card Included

Catching Sunsets on the Bay

The Cooper House in Charlestown, MD

Chesapeake Bay Retreat W/Breathtaking Views

Newly built Tiny House in Historic Kennett Square
Private house rentals

Waterfront Paradise w/ Pier - kayak to Chestertown

Two bedroom small ranch with beautiful forest view

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

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Boho River Cottage

Hill Top Cottage with Chickens!

The Keithley House

Riverside Retreat: Port Deposit w Boat Slip
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
€ 138 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
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
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Jersey Shore Holiday rentals
- Outer Banks Holiday rentals
- Ocean City Holiday rentals
- The Hamptons Holiday 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