Compare Chesapeake Villas

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Featured Villas in Chesapeake

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

At this villa, guests have access to a garden.

Kitchen

Pet friendly

Diamond Resorts Beach Quarters Resort - Ocean Front Studio

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

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

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

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

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

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

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

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

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

$82 nightly

$96 total

Mar 2 - Mar 3

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

$80 nightly

$94 total

Mar 1 - Mar 2

Total with taxes and fees

8.8/10 Excellent! (1,022 reviews)

Fairfield Inn and Suites By Marriott Chesapeake

1560 Crossways Blvd Chesapeake VA

$89 nightly

$104 total

Mar 8 - Mar 9

Total with taxes and fees

9/10 Wonderful! (1,000 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	73 Villas
Lowest Price	$94
Highest Price	$104
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