Chesapeake City Holiday Homes

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Featured Holiday Homes in Chesapeake City

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville MD

Stay at this beach holiday home in Perryville. Enjoy free Wi-Fi, a beach locale and a water park. Popular attractions Craft Haven Marina and Chestnut Point Estates and Marina are located nearby.

Hot tub

Kitchen

Beachfront Sunsets on the Water at Oakwood Beach

Salem NJ

Stay at this beach holiday home in Salem. Enjoy free Wi-Fi, a beach locale and a fitness centre. Popular attractions Hickory Island and Fort Delaware State Park are located nearby.

Kitchen

Washing machine

* NEWLY RENOVATED** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville MD

Stay at this holiday home in Perryville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Chestnut Point Estates and Marina and Craft Haven Marina are located nearby.

Hot tub

Kitchen

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City MD

Stay at this holiday home in Chesapeake City. Enjoy a garden, laundry facilities and furnished patios. Popular attractions Chesapeake City Bridge and C and D Canal Museum are located nearby.

Kitchen

Washing machine

Chesapeake Bay House with Dock & Private Beach

Elkton MD

Stay at this beach holiday home in Elkton. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Chesland Park and Brantwood Park are located nearby.

Kitchen

Washing machine

Luxury Waterfront Home Built for Entertaining!

Abingdon MD

NZ$1,431

15 Dec - 16 Dec

includes taxes & fees

Stay at this holiday home in Abingdon. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Belcamp Beach and Cedar Lane Regional Park are located nearby.

Washing machine

Dryer

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton MD

NZ$489

15 Dec - 16 Dec

includes taxes & fees

Stay at this family-friendly holiday home in Elkton. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Elk Forest Wildlife Management Area and Upper Bay Museum are located nearby.

Kitchen

Washing machine

Modern cozy get-away* game room-amish country

North East MD

Stay at this holiday home in North East. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Calvert Regional Park and Milburn Stone Theater are located nearby.

Kitchen

Washing machine

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Havre De Grace MD

Stay at this family-friendly holiday home in Havre De Grace. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Susquehanna Museum at the Lock House and Havre de Grace Maritime Museum are located nearby.

Kitchen

Washing machine

Wilmington Comfort 4 Min to Riverfront fenced yard

Wilmington DE

Stay at this family-friendly holiday home in Wilmington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wilmington Riverwalk and Christiana Mall are located nearby.

Hot tub

Kitchen

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville MD

NZ$1,043

15 Dec - 16 Dec

includes taxes & fees

Stay at this family-friendly holiday home in Perryville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Chestnut Point Estates and Marina and Craft Haven Marina are located nearby.

Kitchen

Washing machine

A Cool Place to Stay in Wilmington DE

Wilmington DE

Stay at this holiday home in Wilmington. Enjoy air conditioning. Popular attractions Wilmington Riverwalk and Christiana Mall are located nearby.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Holiday Accommodation Chesapeake City

You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chesapeake City are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chesapeake City itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.

Chesapeake City holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.

If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chesapeake City, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.

Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chesapeake City with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.