Stockbridge vacation rentals

We found 675 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 31 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.

Sign in and earn OneKeyCash for your eligible stays

Find spaces that suit your style

  • 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:

  • 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)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)
  • Wyndhurst Golf & Club (4.7 mi / 7.6 km)
  • Kennedy Park (6.8 mi / 10.9 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)
  • The Mount (3.8 mi / 6.2 km)
  • Housatonic River Walk (6.6 mi / 10.6 km)
  • October Mountain State Forest (8.9 mi / 14.3 km)
  • Pittsfield State Forest (13.7 mi / 22 km)
  • Bash Bish Falls State Park (15.1 mi / 24.3 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 houses. Prefer something different? Vrbo has a variety of options to match our guests' unique requirements, so you'll see properties in all shapes and sizes. The perfect fit is waiting for you — lock in yours today.

How much does it cost to rent a vacation rental in Stockbridge?

Season, length of stay and property type are some factors that can affect the price of a vacation home. Simply click on your dates of travel to find your ideal fit. From quaint country cottages to expansive villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Stockbridge?

The average price for a vacation rental near the beach in Stockbridge depends on when you're traveling and the size and type of property you want. You can easily and quickly find prices on Vrbo by entering your destination and travel dates. Then make use of the filter tool to select the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Stockbridge?

You're in luck! There are. You can choose from 53 vacation rentals that allow pets in Stockbridge. Many of our pet-friendly vacation rentals even come with an area outdoors for your fur child to have fun in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Stockbridge?

Add a new level of fun to your trip by booking your group into one of the seven houses with a private pool in Stockbridge. Use our search filter to find properties with pools on Vrbo, then spend lazy days frolicking in a swimming pool that's all yours.

What are popular rental amenities in Stockbridge?

Some of the most popular rental amenities people look for in Stockbridge include a firepit, a nearby river and a lake view. Whether you're going on vacation with your besties, family or even pets, Vrbo vacation properties provide the best amenities for starting a new adventure with the people closest to you.

Are there large group vacation rentals in Stockbridge?

Stockbridge has five vacation properties that can fit 10 or more people. These properties come with all the space you need to enjoy good times with loved ones.

Are there vacation rentals in Stockbridge that welcome kids?

Gather your whole crew for the adventure of a lifetime in Stockbridge at one of our 52 family-friendly vacation rentals. These stays feature amenities that are ideal for trips with the little ones, including laundries, bunk beds and outdoor spaces. Simply click on the "Properties good for families" filter box and select your favorite.

What are the top attractions for families in Stockbridge?

Keep the kids busy at these awesome family-friendly attractions in Stockbridge:

  • Berkshire Scenic Railway Museum
  • Norman Rockwell Museum
  • October Mountain State Forest

Can I find two-bedroom vacation rentals in Stockbridge?

Select from 14 two-bedroom rentals in Stockbridge. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's a spot for whoever's lucky enough to be joining your journey.

Are there vacation rentals with WiFi in Stockbridge?

Whether you want to keep up with the headlines, look over emails or surf your social networks, there are 25 vacation homes with WiFi in Stockbridge. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Stockbridge?

You can pick from 49 Vrbo vacation homes with air conditioning in Stockbridge providing that cooling breeze and extra element of comfort. Just enter your dates of travel and then take advantage of our filter tool to help you locate properties with air conditioning.

More Vacation Rentals ideas

People also search for