Compare Stockbridge Condo Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Stockbridge Condo Rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $141 total per night
$141 total
Jan 13 - Jan 14
Total with taxes and fees
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 access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom

Hancock MA
Guests of this condo enjoy access to ski-in/ski-out access, laundry facilities, and barbecue grills. Staff members can help with accommodation requests, and provide concierge services.
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Hancock MA
This condo features a gym and laundry facilities.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

Hancock MA
Guests staying at this condo enjoy access to ski-in/ski-out access, a gym, and a hot tub. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this ski condo building include laundry facilities and local meal delivery service.
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock MA
$302 nightly
The price is $337 total per night
$337 total
Jan 13 - Jan 14
Total with taxes and fees
At this condo, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free condo building also has a garden.
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox MA
Guests staying at this condo enjoy a sauna, laundry facilities, and barbecue grills.
Pool
Kitchen
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 2

Hancock MA
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 hot tub, laundry facilities, and local meal delivery service.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

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

Hancock MA
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 hot tub, an arcade/game room, and laundry facilities.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Hancock MA
Guests of this condo enjoy features like a gym, a hot tub, and laundry facilities.
Don't see what you're looking for?
See all available properties in Stockbridge
View all properties
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 Stockbridge

    The Red Lion Inn

    The Red Lion Inn

    30 Main Street Stockbridge MA
    $182 nightly
    The price is $204 total per night from Jan 20 to Jan 21
    $204 total
    Jan 20 - Jan 21
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

    26 Glendale Road, RR 183 Stockbridge MA
    $414 nightly
    The price is $462 total per night from Jan 25 to Jan 26
    $462 total
    Jan 25 - Jan 26
    Total with taxes and fees
    9.2/10 Wonderful! (85 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $126 nightly
    The price is $141 total per night from Jan 13 to Jan 14
    $141 total
    Jan 13 - Jan 14
    Total with taxes and fees
    8.6/10 Excellent! (2,202 reviews)

Luxury Condos

Find luxury condos in Stockbridge
Get your vacation off to a fabulous start by booking a luxury condo in Stockbridge. 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 Stockbridge 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 Stockbridge 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.

Stockbridge Condo Rentals essential information

Accommodation
43 Condo Rentals
Lowest Price
$141
Highest Price
$462
Popular accommodation
Vacation Village in the Berkshires, Club Wyndham Bentley Brook Resort - 2 Bedroom, Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool , SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!, 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7, Tranquil Lakeside Escape in the Berkshires, 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, Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths