
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

Cozy SFH for Active Adults

Breathtaking Waterfront Now booking Fall 2025

Historic Victorian Queen Chesapeake City

Rockfish Keeper

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

Chesapeake Waterfront Retreat W/Pool.

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

Waterfront Paradise w/ Pier - kayak to Chestertown

Fair Hill East

Waterfront Paradise on the Bay

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Chesapeake Bay Retreat W/Breathtaking Views

The Cooper House in Charlestown, MD

High Tide & Hound

The Fishing Factory
Private house rentals

Aberdeen Waterfront Retreat Easy Drive from I95

The Sunset House

~Cedar Hill Cottage~

Two bedroom small ranch with beautiful forest view

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

The Beach House

A home away from home.

Cute, cozy and convenient 2BR w/ office
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ588 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 Vacation rentals
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- Long Island Vacation rentals
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- Outer Banks Vacation rentals
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- Ocean City Vacation rentals
- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- M&T Bank Stadium
- Fortescue Beach
- Oriole Park at Camden Yards
- Fairmount Park
- Longwood Gardens
- Dutch Wonderland
- Betterton Beach
- Penn's Landing
- Hampden
- Sandy Point State Park
- Philadelphia Museum of Art
- 30th Street Station
- Patterson Park
- Marsh Creek State Park
- French Creek State Park
- Aronimink Golf Club
- Philadelphia Zoo
- The Franklin Institute
- Big Stone Beach
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD