Compare The Berkshires Condo Rentals

Featured The Berkshires Condo Rentals

Free Cancellation

Reserve now, pay when you stay

$169

per night

Apr 20 - Apr 21

Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with concierge services and access to locker space. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.

Fireplace

Pool

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

At this condo, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. Other amenities at this ski condo building include a spa tub and an arcade/game room.

Hot Tub

Pool

Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe

This condo features ski-in/ski-out access, an indoor pool, and a gym. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this ski condo building include a sauna, a spa tub, and an arcade/game room.

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

This condo features ski-in/ski-out access, an outdoor pool, and a gym. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this ski condo building include a spa tub and local meal delivery service.

Hot Tub

Fireplace

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

At this condo, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this ski condo building include a spa tub, an arcade/game room, and local meal delivery service.

Hot Tub

Fireplace

Wyndham Bentley Brook! 2 Bd. dlx. in Hancock

This condo features ski-in/ski-out access, an indoor pool, and a gym. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this ski condo building include a sauna, a spa tub, and an arcade/game room.

Mountainside Condo @ Jiminy Peak in the Berkshires

This condo is a smoke-free condo building.

Fireplace

Washer

Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd.

This condo features ski-in/ski-out access, an indoor pool, and a gym. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this ski condo building include a sauna, a spa tub, and an arcade/game room.

Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.

Guests of this condo enjoy ski-in/ski-out access, an indoor pool, and a gym. Friendly staff can provide concierge services, and also offer advice about sightseeing. Other amenities at this ski condo building include a sauna, a spa tub, and an arcade/game room.

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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.

The Berkshires Accommodation Oceanfront

The Black Swan Lee - Lenox, Ascend Hotel Collection

435 Laurel St, Lee, MA

$94

per night

Apr 21 - Apr 22

8.8/10 Excellent! (1,000 reviews)

Hotel Options in The Berkshires

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

$110

per night

Apr 21 - Apr 22

9/10 Wonderful! (222 reviews)

The Red Lion Inn

30 Main Street, Stockbridge, MA

$99

per night

Apr 30 - May 1

8.8/10 Excellent! (865 reviews)

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

$101

per night

Apr 25 - Apr 26

9/10 Wonderful! (1,000 reviews)

Luxury Condos

Find luxury condos in The Berkshires
Get your vacation off to a fabulous start by booking a luxury condo in The Berkshires. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a The Berkshires condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.

Exploring The Berkshires will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

The Berkshires Condo Rentals essential information

Accommodation	39 Condo Rentals
Lowest Price	$94
Highest Price	$169
Popular accommodation	Vacation Village in the Berkshires, Ski-In/Ski-Out at Jiminy Peak in the Country Inn, Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2, SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1, Wyndham Bentley Brook! 2 Bd. dlx. in Hancock, Mountainside Condo @ Jiminy Peak in the Berkshires, Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd., Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.