Chesapeake City Holiday Rentals
Check Chesapeake City holiday rental availability
Holiday Rentals in Chesapeake City
Historic Chesapeake City Stay
Chesapeake City Overlook: Breathtaking View!
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Oaxaca, a private room with private entrance
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Beachfront Sunsets on the Water at Oakwood Beach
Quarry Landing - Center of Town & River View - 3 Bedroom
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Historic home in the heart of Main Street- walkable to shops and restaurants
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Guest Suite for up to 2 in a Victorian on the Chester River
Other types of properties in Chesapeake City you may be interested in
Sonesta Select Newark Christiana Mall
Red Roof Inn & Suites Newark - University
Comfort Inn & Suites Newark - Wilmington
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesapeake City holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesapeake City. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesapeake City. Seeing all the best attractions is bound to make you fall in love with Chesapeake City. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesapeake City short-term rentals, that won’t be hard to do.
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