Destination guide

The historic city of Stockbridge awaits you

Come and experience Stockbridge and its museums, history and architecture. 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

Activities and attractions in Stockbridge

Are you searching for things to do during your stay? Venture out of your cozy vacation rental and experience everything that makes Stockbridge a fun spot to vacation. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Greenock Country Club (3.3 mi / 5.3 km)
  • Wood's Pond (5.5 mi / 8.8 km)
  • Pleasant Valley Wilderness Sanctuary (6.6 mi / 10.6 km)
  • Kennedy Park (6.8 mi / 10.9 km)
  • Ski Butternut (7.2 mi / 11.7 km)
  • Furnace Brook Winery at Hilltop Orchards (8.1 mi / 13 km)
Natural features

Exploring the natural landscape of Stockbridge

Whether you're an outdoor enthusiast or just want to take in the scenery, Stockbridge is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Berkshire Botanical Garden (1.3 mi / 2.1 km)
  • Beartown State Forest (4.2 mi / 6.7 km)
  • Tyringham Cobble (5.1 mi / 8.2 km)
  • Wood's Pond (5.5 mi / 8.8 km)
  • Lake Mansfield Park (6.3 mi / 10.1 km)
  • Goose Pond Reservation (6.7 mi / 10.7 km)
How to get there

Traveling to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.5 mi (15.4 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Hudson, NY (HCC-Columbia County), which is 20.2 mi (32.5 km) away.

Can I find a vacation rental around Stockbridge?

Yes, our 2019 property listings offer a large selection of 574 vacation rentals near Stockbridge. From 379 Houses to 63 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Stockbridge for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Stockbridge?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Stockbridge:

  • Copake Lake: 31 vacation rentals
  • Lee: 619 vacation rentals
  • South Lee: 15 vacation rentals
  • Housatonic: 416 vacation rentals
  • Falls Village: 151 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Stockbridge?

HomeAway offers a large selection of vacation rentals near lovely places in Stockbridge. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • National Shrine of the Divine Mercy: 794 vacation rentals
  • Norman Rockwell Museum: 783 vacation rentals
  • Chesterwood: 776 vacation rentals
  • Berkshire Theatre Festival: 759 vacation rentals
  • Berkshire Botanical Garden: 816 vacation rentals

But there are many other points of interest around Stockbridge listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Stockbridge?

Yes, of course. HomeAway has 379 Houses in Stockbridge. Our other popular types of vacation rentals in Stockbridge include:

  • Cottages: 63 rentals available
  • Cabins: 63 rentals available
  • Condos/Apartments: 46 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Farmhouses and more.

Can I find a vacation rental with pool in Stockbridge?

Yes, you can select your preferred vacation rental with pool among our 88 vacation rentals with pool available in Stockbridge. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Stockbridge