Chesapeake Holiday Rentals
Holiday Rentals in Chesapeake
The Atrium Resort by VSA Resorts
The Ocean Sands Resort by VSA Resorts
The Ocean Key Resort by VSA Resorts
Beach Condo 2 Min Walk From The Beach
Beach Condo, Walk To The Beach
The Art Door only minutes from beach
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
Cozy Suite at the Beach
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
Angie's Guest Cottage
Lovely 4-bedroom open concept home 8mins from oceanfront
Great Location ! 1 Short Block To The Boardwalk.
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Norfolk Beach Cottage Rental
SPRING SPECIAL !!!Canal Front - Paddle Board
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Entire home on Bells Island in Currituck County NC
Other types of properties in Chesapeake you may be interested in
Comfort Suites Chesapeake - Norfolk
Wingate by Wyndham Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
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 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. 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. Seeing all the best attractions is bound to make you fall in love with Chesapeake. 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 short-term rentals, that won’t be hard to do.
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