Stockbridge holiday homes

We found 727 holiday rentals — enter your dates for availability

Discover a selection of 25 homes and other holiday rentals in Stockbridge that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The historical city of Stockbridge awaits you

Enjoy the area's museums, history and architecture with a rental holiday home in Stockbridge. Revered 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 attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Stockbridge has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wyndhurst Golf & Club (4.7 mi / 7.6 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)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)
  • Kennedy Park (6.8 mi / 10.9 km)

Exploring the natural features in Stockbridge

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Stockbridge. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre. 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 holiday home accommodation in Stockbridge?
The most sought-after types of holiday homes in Stockbridge are houses. Prefer something different? Bookabach 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 holiday home in Stockbridge?
Season, length of stay and property type are some factors that can affect the price of a holiday home. Simply click on your dates of travel to find your ideal fit. From quaint country cottages to expansive villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Stockbridge?
The average price for a holiday home near the beach in Stockbridge depends on when you’re travelling and the size and type of property you want. You can easily and quickly find prices on Bookabach 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 holiday homes in Stockbridge?
You’re in luck! There are. You can choose from 53 holiday homes that allow pets in Stockbridge. Many of our pet-friendly holiday homes 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 Bookabach.
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 Bookabach, then spend lazy days frolicking in a swimming pool that’s all yours.
What are popular home amenities in Stockbridge?
Some of the most popular home amenities people look for in Stockbridge include a firepit, a nearby river and a lake view. Whether you’re going on holiday with your besties, family or even pets, Bookabach holiday properties provide the best amenities for starting a new adventure with the people closest to you.
Are there large group holiday homes in Stockbridge?
Stockbridge has five holiday 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 holiday homes in Stockbridge that welcome kids?
Gather your whole crew for the adventure of a lifetime in Stockbridge at one of our 52 family-friendly holiday homes. 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 favourite.
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 holiday homes in Stockbridge?
Select from 14 two-bedroom homes 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 holiday homes with WiFi in Stockbridge?
Whether you want to keep up with the headlines, look over emails or surf your social networks, there are 25 holiday homes with WiFi in Stockbridge. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Stockbridge?
You can pick from 49 Bookabach holiday 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.
How old do you have to be to rent a holiday home in Stockbridge?
Age restrictions can vary across properties on Bookabach, so be sure to look at the rules of the holiday home in Stockbridge you want to book. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Stockbridge for?
The amount of time you can stay in a Stockbridge holiday home for is down to each property. Simply tap in your travel dates to view available options that offer extended stays. They include everything you need to make your extended trip more convenient and enjoyable, like kitchens and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.

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