Compare Stockbridge Vacation 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

Stockbridge Rentals

The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
3.11 mi from city center
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
The Kemble- Built by a US Secretary of State in Lenox

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

5.02 mi from city center
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
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

5.37 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

3.95 mi from city center
$735 nightly
The price is $821 total per night
$821 total
Oct 21 - Oct 22
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Washer
Dryer
Peace and quiet on the lake

Peace and quiet on the lake

13.29 mi from city center
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

16.38 mi from city center
At this vacation home, guests have access to a garden.
Air conditioning
Outdoor Space
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

17.62 mi from city center
$1,026 nightly
The price is $1,111 total per night
$1,111 total
Oct 21 - Oct 22
Total with taxes and fees
This vacation home features a hot tub, an arcade/game room, and a library. Other amenities at this family-friendly vacation home include laundry facilities and barbecue grills.
Hot Tub
Kitchen
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

18.59 mi from city center
$469 nightly
The price is $475 total per night
$475 total
Oct 6 - Oct 7
Total with taxes and fees
This vacation home offers a gym, a sauna, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd, Hancock, MA
Free Cancellation
Reserve now, pay when you stay
18.74 mi from city center
$149 nightly
The price is $166 total per night
$166 total
Oct 19 - Oct 20
Total with taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and tours or tickets. Other amenities at this ski condominium resort include 2 hot tubs, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub
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
19.22 mi from city center
$86 nightly
The price is $96 total per night
$96 total
Nov 2 - Nov 3
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 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.
Pool
Parking included
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

16.67 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly vacation home include a library, laundry facilities, and a garden.
Pool
Kitchen
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
19.71 mi from city center
$98 nightly
The price is $109 total per night
$109 total
Oct 6 - Oct 7
Total with taxes and fees
Guests staying at Huttopia Berkshires enjoy an outdoor pool, free WiFi in public areas, and a picnic area. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours.
Pool
Pet friendly
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.

Stockbridge Large Group Rentals

How to Book Vacation Rentals in Stockbridge



🏠 What is the best price for Stockbridge vacation rentals?

Stockbridge vacation rentals range in price, starting at $96 per night.


🏠 What types of vacation rentals in Stockbridge can I rent?

Orbitz offers a wide range of Stockbridge rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Stockbridge condo rentals.


🏠 Is it free to cancel my Stockbridge vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Stockbridge vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Stockbridge. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Stockbridge?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Stockbridge apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Stockbridge?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Stockbridge package deals will get you even more savings.

More to Explore

More to Explore