
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

Breathtaking waterfront home- booking Winter 2025

Historic Victorian Queen Chesapeake City

Rockfish Keeper

The Mariner's House

Holly Point on the Water

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

Lark's Nest on the Chester River

Connection Pointe•River views•Quiet•Peaceful

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

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

Catching Sunsets on the Bay

The Cooper House in Charlestown, MD

Boho River Cottage

Newly built Tiny House in Historic Kennett Square
Private house rentals

The Sunset House

Two bedroom small ranch with beautiful forest view

Stay Anchored Chesapeake Bay, 5 bedrooms, 3 bath

Water View Historic B & B - Gift Card Included

Chesapeake Bay Retreat W/Breathtaking Views

Ruby's Sea Glass Cottage near Betterton Beach

Cute, cozy and convenient 2BR w/ office

Waldins Chesapeake
Quick stats about house rentals in Chesapeake City
Total rentals
10 properties
Nightly prices starting at
$207 SGD 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
- Jersey Shore Holiday rentals
- Mount Pocono 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
- Fairmount Park
- Oriole Park at Camden Yards
- Longwood Gardens
- Betterton Beach
- Penn's Landing
- Hampden
- Philadelphia Museum of Art
- Sandy Point State Park
- 30th Street Station
- Patterson Park
- Marsh Creek State Park
- French Creek State Park
- Aronimink Golf Club
- Philadelphia Zoo
- Big Stone Beach
- The Franklin Institute
- Wissahickon Valley Park
- Crystal Beach Manor, Earleville, MD
- Wells Fargo Center