Compare Chesapeake Villas

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Featured Villas in Chesapeake

The Boat House on the Bay - On the water; Pet Friendly; WiFi

The Boat House on the Bay - On the water; Pet Friendly; WiFi

Norfolk VA
At this villa, guests have access to a garden.
Kitchen
Pet friendly
Diamond Resorts Beach Quarters Resort - Ocean Front Studio

Diamond Resorts Beach Quarters Resort - Ocean Front Studio

2 out of 5
Virginia Beach VA
Guests of this villa enjoy features like a hot tub. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Pool
Hot Tub
Diamond Resorts Oceanaire Resort - Studio with Ocean View Balcony

Diamond Resorts Oceanaire Resort - Studio with Ocean View Balcony

Virginia Beach VA
Guests of this villa have access to a hot tub. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Pool
Hot Tub
Diamond Resorts Ocean Beach Club - Studio - Ocean Front

Diamond Resorts Ocean Beach Club - Studio - Ocean Front

Virginia Beach VA
This villa features a hot tub and an arcade/game room. Staff members can help with accommodation requests, and provide concierge services.
Pool
Hot Tub
Diamond Resorts Ocean Beach Club - 1 Bedroom Suite - No Balcony

Diamond Resorts Ocean Beach Club - 1 Bedroom Suite - No Balcony

Virginia Beach VA
Guests of this villa have access to a hot tub. Staff members can answer questions about accommodations, and also provide concierge services.
Pool
Hot Tub
Diamond Resorts Ocean Beach Club - Studio

Diamond Resorts Ocean Beach Club - Studio

Virginia Beach VA
Guests of this villa have access to a hot tub. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Pool
Hot Tub
Old-World Retreat at 1860s Manor: Luxury Amenities - Tennis Court & Nature Trail

Old-World Retreat at 1860s Manor: Luxury Amenities - Tennis Court & Nature Trail

Virginia Beach VA
$302 nightly
The price is $349 total per night
$349 total
Jan 12 - Jan 13
Total with taxes and fees
At this villa, guests have access to features like laundry facilities. This family-friendly villa also has a garden.
Kitchen
Washer
Diamond Resorts Turtle Cay Resort - 2 Bedroom Lockoff

Diamond Resorts Turtle Cay Resort - 2 Bedroom Lockoff

Virginia Beach VA
At this villa, guests have access to a hot tub. Staff members can answer questions about accommodations, and also provide concierge services.
Pool
Hot Tub
Diamond Resorts Turtle Cay Resort - Studio

Diamond Resorts Turtle Cay Resort - Studio

Virginia Beach VA
A gym and a hot tub are features at this villa. Staff members can help with accommodation requests, and provide concierge services.
Pool
Hot Tub
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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.

Hotel Options in Chesapeake

    Comfort Suites Chesapeake - Norfolk

    Comfort Suites Chesapeake - Norfolk

    1550 Crossways Blvd Chesapeake VA
    $70 nightly
    The price is $82 total per night from Jan 11 to Jan 12
    $82 total
    Jan 11 - Jan 12
    Total with taxes and fees
    8.4/10 Very Good! (1,018 reviews)
    Wingate by Wyndham Chesapeake

    Wingate by Wyndham Chesapeake

    817 Greenbrier Circle Chesapeake VA
    $75 nightly
    The price is $88 total per night from Jan 18 to Jan 19
    $88 total
    Jan 18 - Jan 19
    Total with taxes and fees
    7.8/10 Good! (1,006 reviews)
    Holiday Inn Express Chesapeake - Norfolk by IHG

    Holiday Inn Express Chesapeake - Norfolk by IHG

    721 Conference Center Drive Chesapeake VA
    $83 nightly
    The price is $97 total per night from Jan 25 to Jan 26
    $97 total
    Jan 25 - Jan 26
    Total with taxes and fees
    8.6/10 Excellent! (1,003 reviews)

Luxury Villas

Book luxury villas in Chesapeake
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chesapeake. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Chesapeake, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Chesapeake
You won’t have a problem finding your own space in Chesapeake. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Chesapeake on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Chesapeake rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Chesapeake Villas essential information

Accommodation
111 Villas
Lowest Price
$82
Highest Price
$349
Popular accommodation
The Boat House on the Bay - On the water; Pet Friendly; WiFi, Diamond Resorts Beach Quarters Resort - Ocean Front Studio, Diamond Resorts Oceanaire Resort - Studio with Ocean View Balcony, Diamond Resorts Ocean Beach Club - Studio - Ocean Front, Diamond Resorts Ocean Beach Club - 1 Bedroom Suite - No Balcony, Diamond Resorts Ocean Beach Club - Studio, Old-World Retreat at 1860s Manor: Luxury Amenities - Tennis Court & Nature Trail, Diamond Resorts Turtle Cay Resort - 2 Bedroom Lockoff, Diamond Resorts Turtle Cay Resort - Studio

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