Stockbridge vacation rentals

We found 725 vacation rentals — enter your dates for availability

Discover a selection of 25 homes and other vacation rentals in Stockbridge that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as WiFi and cable TV. What you'll find is a rental that has what everyone needs, including options that are accessible or non-smoking.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

The historic city of Stockbridge awaits you

Enjoy the area's museums, history and architecture and make a vacation rental your home during your stay in Stockbridge. Well-liked for its gardens, camping and hiking, this city is both romantic and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Stockbridge

Are you looking for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Stockbridge a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Wyndhurst Golf & Club (4.7 mi / 7.6 km)
  • Kennedy Park (6.8 mi / 10.9 km)
  • Ski Butternut (7.2 mi / 11.6 km)
  • Bousquet Ski Area (9.1 mi / 14.6 km)
  • Catamount Ski Area (11.6 mi / 18.7 km)
  • Otis Ridge (12.9 mi / 20.8 km)

Exploring the natural features in Stockbridge

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Stockbridge. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Naumkeag Museum (0.3 mi / 0.4 km)
  • Berkshire Botanical Garden (1.2 mi / 2 km)
  • The Mount (3.8 mi / 6.2 km)
  • Lake Mansfield Park (6.2 mi / 9.9 km)
  • Housatonic River (6.6 mi / 10.5 km)
  • Housatonic River Walk (6.6 mi / 10.6 km)

Transportation options to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.6 mi (15.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Stockbridge?
The most sought-after types of vacation rentals in Stockbridge are cottages. Hoping for something different? Vrbo has many options to match our guests’ unique needs, so you’ll see vacation homes in all sizes and shapes. The ideal home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a vacation rental in Stockbridge?
Property type, length of stay and time of year are some of the conditions that can determine the price of a vacation home. Simply enter your dates of travel to find your dream escape. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals offer unbeatable value.
How much does it cost to rent a beach house in Stockbridge?
The average price for a vacation home by the beach in Stockbridge will depend on when you’re going and the type and size of property you’re looking for. Find prices quickly and easily on Vrbo by entering your dates of travel. Then use the handy filter tool to choose the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in Stockbridge?
Yes. There are. You can choose from 53 vacation homes that roll out the welcome mat in Stockbridge on Vrbo. Our cuddly best friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect property where Rover can get in on the family fun.
Can I rent a house with a pool in Stockbridge?
Pack your swimwear and inflatable unicorn, because there are nine houses with a private pool in Stockbridge. Base yourself at one of these terrific vacation rentals and enjoy a pool day every day. Simply enter your dates into Vrbo, then use the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Stockbridge?
A lake view, a water view and a garden head the list of most popular rental amenities in Stockbridge. Whether you’re taking a trip as a party of one, with your significant other or as a family group, Vrbo can help you find a vacation rental that fits your style with all the features you need.
Are there large group vacation rentals in Stockbridge?
You can pick from six vacation properties in Stockbridge that can accommodate 10 or more guests. Whether you’re planning time away with extended family or an event like an anniversary, there’s ample room to get your group together under the same roof.
Are there vacation rentals in Stockbridge that welcome kids?
Stockbridge has 52 family-friendly vacation homes to pick from. And tracking down a stay that welcomes kids is simple with Vrbo’s “Properties good for families” filter. Besides having the entire place to yourselves, you’ll get access to perks and amenities like dining rooms, yards and private pools.
What are the top attractions for families in Stockbridge?
There’s a ton of cool things to see and do with the family in Stockbridge, such as:

  • National Shrine of the Divine Mercy
  • Norman Rockwell Museum
  • Naumkeag Museum

Can I find two-bedroom vacation rentals in Stockbridge?
Take your pick of 15 two-bedroom vacation rentals in Stockbridge. Give your little ones the second room or maybe fill it with a couple of your nearest and dearest friends. There’s space for whoever’s lucky enough to be coming along for the ride.
Are there vacation rentals with WiFi in Stockbridge?
You’ll find 24 vacation rentals with WiFi in Stockbridge. If you want to disconnect from the world during your escape, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Stockbridge?
Pick from 50 vacation rentals with air conditioning in Stockbridge offering that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our handy filters to find stays with air conditioning.
How old do you have to be to rent a vacation rental in Stockbridge?
The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, so check the rules of your preferred Stockbridge stay before booking.
How long can I rent a vacation rental in Stockbridge for?
It’s up to the Stockbridge property. To look at a list of options offering extended stays, simply type your travel dates and number of guests into the Vrbo search page. You can enjoy having the whole place to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and a backyard where the kids can burn off energy. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Stockbridge?
Overnight trip or extended vacation, Vrbo has some exclusive deals and discounted options in Stockbridge that’ll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the perfect place to stay — without draining your wallet.

More Vacation Rentals ideas

People also search for