Compare Hillsdale Villas

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Featured Villas in Hillsdale

The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Guests of this villa enjoy features like a gym, a sauna, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Catskill Villa/Pool with Hudson River View

Catskill Villa/Pool with Hudson River View

At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson

5k+ Sq Ft of Luxury Living on 54 Acres near Hudson

Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.
Pool
Hot Tub
Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game

At this villa, guests have access to an arcade/game room, laundry facilities, and a garden.
Washer
Dryer
Secluded Art & Architecture in Nature Retreat - hi

Secluded Art & Architecture in Nature Retreat - hi

At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Kitchen
Washer
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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 Hillsdale

    Life House Berkshires

    Life House Berkshires

    194 Pittsfield Rd, Lenox, MA
    The price is $119 per night from May 4 to May 5
    $119
    includes taxes & fees
    $107 per night
    May 4 - May 5
    9/10 Wonderful! (563 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    The price is $134 per night from Apr 28 to Apr 29
    $134
    includes taxes & fees
    $120 per night
    Apr 28 - Apr 29
    9/10 Wonderful! (620 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd, Lenox, MA
    The price is $108 per night from Apr 28 to Apr 29
    $108
    includes taxes & fees
    $97 per night
    Apr 28 - Apr 29
    9/10 Wonderful! (1,002 reviews)

Luxury Villas

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

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

A top-end villa experience in Hillsdale 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!

Villas in Hillsdale

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