Compare Pittsfield Villas

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Featured Villas in Pittsfield

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

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

Lenox MA
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, a garden, and barbecue grills.
Kitchen
Washer
Serene Farmhouse Villa: Pool + Hot Tub and Grill

Serene Farmhouse Villa: Pool + Hot Tub and Grill

Chatham NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
Vermont Vacation Villa—Grapevine Getaway

Vermont Vacation Villa—Grapevine Getaway

Pownal VT
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
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 Pittsfield

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $99 nightly
    The price is $110 total per night from Dec 7 to Dec 8
    $110 total
    Dec 7 - Dec 8
    Total with taxes and fees
    9/10 Wonderful! (763 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    Holiday Inn & Suites Pittsfield-Berkshires by IHG

    One West Street Pittsfield MA
    $89 nightly
    The price is $100 total per night from Nov 29 to Nov 30
    $100 total
    Nov 29 - Nov 30
    Total with taxes and fees
    7.8/10 Good! (962 reviews)
    Hotel On North

    Hotel On North

    297 North Street Pittsfield MA
    $133 nightly
    The price is $149 total per night from Dec 22 to Dec 23
    $149 total
    Dec 22 - Dec 23
    Total with taxes and fees
    9.4/10 Exceptional! (797 reviews)

Luxury Villas

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

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

A top-end villa experience in Pittsfield 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!

Pittsfield Villas essential information

Accommodation
3 Villas
Lowest Price
$100
Highest Price
$149
Popular accommodation
The Kemble- Built by a US Secretary of State in Lenox, Serene Farmhouse Villa: Pool + Hot Tub and Grill, Vermont Vacation Villa—Grapevine Getaway