
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 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

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.

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

Aberdeen Waterfront Retreat Easy Drive from I95

The Lighthouse

Arden Cottage w/ Creek + Trails | Dogs OK

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

Chesapeake Bay Retreat W/Breathtaking Views

Stay-4-Awhile

Ruby's Sea Glass Cottage near Betterton Beach

Cute, cozy and convenient 2BR w/ office
Private house rentals

~Cedar Hill Cottage~

Spacious, Quiet & Peaceful

Waterfront Paradise w/ Pier - kayak to Chestertown

Waterfront Paradise on the Bay

High Tide & Hound

A home away from home.

Cheerful and Cozy Charming Home

Lotus House: spacious, private, expansive views
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
$243 AUD 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
Wi-Fi availability
10 properties include access to Wi-Fi
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
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Mount Pocono Holiday rentals
- Outer Banks Holiday rentals
- South Jersey Holiday rentals
- The Hamptons Holiday rentals
- Pennsylvania Convention Center
- Lincoln Financial Field
- Citizens Bank Park
- Fortescue Beach
- M&T Bank Stadium
- 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
- The Franklin Institute
- Philadelphia Zoo
- Wissahickon Valley Park
- Big Stone Beach
- Crystal Beach Manor, Earleville, MD