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Chesapeake vacation rentals

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Top-rated vacation rentals in Chesapeake

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest suite in Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!
$66 per night
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Rental unit in Norfolk
The SEA-clusion III
Enjoy this cozy one-bedroom apartment to yourself. Just a short walk away from Ocean-view beach. Perfect for couples and singles looking for a beach get away or connecting with friends and family, who are serving in the military. We are taking Covid-19 very serious, going above and beyond to protect our guests. All surfaces are cleaned thoroughly including the sitting and living areas.
$62 per night
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Guest suite in Virginia Beach
*New* Studio
Cozy inviting Efficiency Apartment located in the heart of Virginia Beach! Minutes from highway 64. Which gives easy access to anywhere in the Hampton Roads area. 15-20 minute drive to Virginia Beach Ocean front and convention center. 2 minutes from CBN and founders in. Soccer complex, Stumpy lake golf course close by. Restaurants and shopping 5 minutes away.
$70 per night
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Stay near Chesapeake's top sights

Photo of Lynnhaven Mall
Lynnhaven Mall99 locals recommend
Photo of Mount Trashmore Park
Mount Trashmore Park83 locals recommend
Photo of Veterans United Home Loans Amphitheater at Virginia Beach
Veterans United Home Loans Amphitheater at Virginia Beach56 locals recommend
Photo of Greenbrier Mall
Greenbrier Mall25 locals recommend
Photo of Topgolf
Topgolf111 locals recommend
Photo of MacArthur Center
MacArthur Center156 locals recommend

Other great vacation rentals in Chesapeake

Private room in Chesapeake
Warming master bedroom in a lovely full house
$26 per night
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Private room in Chesapeake
⚓Welcome Aboard! ⛱️Relaxation awaits!
$73 per night
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Private room in Chesapeake
Private, Spacious Studio Apartment, Bath, Quiet
$49 per night
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Private room in Chesapeake
Beautiful family's home close to downtown Norfolk
$40 per night
Private room in Ocean View
Comfortable Private Room Navy Base/Ocean View
$44 per night
Private room in Chesapeake
Private Entrance, Spacious Master Bedroom Suite
$49 per night
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Rental unit in Norfolk
Studio couple blocks from the beach
$46 per night
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Private room in Chesapeake
Queen Bed w/ Private Bath & Private Entrance!
$52 per night
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Townhouse in Chesapeake
2BR-1.5 Bath Electric & Vibrant R&R Townhome
$71 per night
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Condo in Ocean View
Lovely 1-bedroom condo! Next to Navy Base & Beach#
$58 per night
Private room in Norfolk
Beautiful Private Room Navy base/ ODU/Downtown
$62 per night
Rental unit in Norfolk
The SEA-clusion 5
$59 per night
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Stays in Downtown Norfolk

Condo in Downtown Norfolk
Best City View Condo in Downtown Norfolk
$107 per night
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Guesthouse in Downtown Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
$120 per night
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Guest suite in Downtown Norfolk
Private Guest House in Historic Downtown
$91 per night
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Guest suite in Downtown Norfolk
Cobblestone street apartment with rooftop views!
$95 per night
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Stays in Ghent

Rental unit in Ghent
The Rosalie Suite 1, Steps from Norfolks Hospitals
$105 per night
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Rental unit in Ghent
Colley Manor - Starboard Suite
$70 per night
Rental unit in Ghent
The Rosalie Suite 3, Steps from Norfolks Hospitals
$103 per night
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Rental unit in Ghent
Lovely Studio in Ghent
$86 per night
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Stays in Olde Towne

Rental unit in Portsmouth
Private 1 Bed Apt - Historic Olde Towne Portsmouth
$80 per night
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Condo in Portsmouth
Cozy Condo in historic district of Olde Towne
$65 per night
Rental unit in Portsmouth
Old Towne Apartment near Rivers Casino
$99 per night
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Rental unit in Portsmouth
Cozy, Private Ground Floor Apt in Historic Home
$95 per night
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