
House holiday rentals in Chesapeake City
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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

Quiet Getaway with pool!

The Mariner's House

Holly Point on the Water

The Hidden Gem•Heated pool•Pickleball Court
Weekly house rentals

Connection Pointe•River views•Quiet•Peaceful

Water View Historic B & B - Gift Card Included

Catching Sunsets on the Bay

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

The Cooper House in Charlestown, MD

Newly built Tiny House in Historic Kennett Square

Ruby's Sea Glass Cottage near Betterton Beach

Gunpowder Retreat
Private house rentals

Aberdeen Waterfront Retreat Easy Drive from I95

~Cedar Hill Cottage~

Lark's Nest on the Chester River

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

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Chesapeake Bay Retreat W/Breathtaking Views

Boho River Cottage

Waterfront w/ Hot Tub + Dock | Harbor View Haven
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