Discover a selection of 479 vacation rentals in Stockbridge, MA, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including pool and internet/wifi. Prices start at C$ 314 per night, and house rentals and cottage rentals are popular options for a stay in Stockbridge. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Stockbridge
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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.

How many vacation rentals are available around Stockbridge?

Our 2021 vacation rental listings offer a large selection of 479 house rentals around Stockbridge. From 389 house rentals to 49 cottage rentals, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Stockbridge is on Vrbo.

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

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

  • Norman Rockwell Museum: 686 home rentals
  • National Shrine of the Divine Mercy: 677 home rentals
  • Schantz Galleries: 671 home rentals
  • Mission House: 676 home rentals
  • Berkshire Theatre Festival: 670 home rentals

But there are many other points of interest around Stockbridge listed on Vrbo Canada 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. Vrbo Canada has 389 Houses in Stockbridge. Our other popular types of vacation rentals in Stockbridge include:

  • Cottages: 49 lodging choices
  • Cabins: 56 lodging choices
  • Condos/Apartments: 39 lodging choices

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

Can I find a vacation rental with pool in Stockbridge?

Yes, you can select your preferred vacation rental with pool among our 73 vacation homes with pool available in Stockbridge.