Compare Chester Villas

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Featured Villas in Chester

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD
At this villa, guests enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and laundry facilities.
Private Peninsula Estate, Pool Houses, Crab Shack

Private Peninsula Estate, Pool Houses, Crab Shack

Neavitt MD
At this villa, guests have access to a gym, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.
Blake House Historic Estate with Private Inn

Blake House Historic Estate with Private Inn

Centreville MD
At this villa, guests have access to a gym, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
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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 Chester

    Graduate by Hilton Annapolis

    Graduate by Hilton Annapolis

    126 West St Annapolis MD
    $147 nightly
    The price is $167 total per night from Oct 26 to Oct 27
    $167 total
    Oct 26 - Oct 27
    Total with taxes and fees
    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    $90 nightly
    The price is $103 total per night from Oct 11 to Oct 12
    $103 total
    Oct 11 - Oct 12
    Total with taxes and fees
    8.8/10 Excellent! (1,237 reviews)
    Crowne Plaza Annapolis by IHG

    Crowne Plaza Annapolis by IHG

    173 Jennifer Rd Annapolis MD
    $110 nightly
    The price is $125 total per night from Oct 11 to Oct 12
    $125 total
    Oct 11 - Oct 12
    Total with taxes and fees
    8.8/10 Excellent! (1,011 reviews)

Luxury Villas

Book luxury villas in Chester
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chester. 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 Chester, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Chester
You won’t have a problem finding your own space in Chester. 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 Chester on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Chester 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!

Chester Villas essential information

Accommodation
3 Villas
Lowest Price
$103
Highest Price
$167
Popular accommodation
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna, Private Peninsula Estate, Pool Houses, Crab Shack, Blake House Historic Estate with Private Inn

More to Explore