Holiday Rentals in Chesapeake
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Holiday Rentals in Chesapeake

The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

stayAPT Suites Suffolk-Chesapeake

Angie's Guest Cottage

Four Sails Resort

Your own private beach with this charming 3-bedroom beachfront house!

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

The Art Door only minutes from beach

Dolphin Run Oceanfront Suites Virginia Beach

The Mayflower - Luxury Beachside Penthouse #1603

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

VB Oceanfront Condo at Boardwalk. See Dolphins from Balcony. Steps to Beach+Pool

Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
Other types of properties in Chesapeake you may be interested in

Holiday Inn Express Chesapeake - Norfolk by IHG
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.