Chesapeake Holiday Homes

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Featured Holiday Homes in Chesapeake

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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

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 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 itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.

Chesapeake 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, 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 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.

Chesapeake Holiday Homes essential information

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1471 Holiday Homes
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Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!, The Anchor ⭐️ 4BR Beach House w Balcony & King Bed, C9083 Cavallo Dunes. Oceanfront, 3 Bedrooms, Hot Tub, Pets OK, 4x4 Area, Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk., Lakefront Oasis Centrally Located. Elegant, spacious and you're going to love it, Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly, July 4th Week SPECIAL Canal Front ADVANCE WELL WATER Pet Friendly PADDLE BOARD, Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (412B), Your own private beach with this charming 3-bedroom beachfront house!, Spacious 4 BR Townhouse Walking Distance to the Beach and Boardwalk (408B), Sandbridge Farmhouse… 1 mile to beach~completely updated & restored~New pool, Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!

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