Discover a selection of 475 holiday rentals in Stockbridge, MA, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 240 per night, and houses and cottages 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 historical city of Stockbridge awaits you

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

Activities and attractions in Stockbridge

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

  • 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 centre:

  • 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

Travelling to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.5 mi (15.4 km) from the city centre. 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 holiday rentals are available around Stockbridge?

Our 2021 accommodation listings offer a large selection of 475 holiday lettings around Stockbridge. From 394 houses to 50 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Stockbridge?

Vrbo UK offers a large selection of holiday accommodations near great places in Stockbridge. From Vrbo UK travellers, the most popular points of interest to stay near are:

  • Berkshire Botanical Garden: 684 holiday lettings
  • Berkshire Theatre Festival: 662 holiday lettings
  • Chesterwood: 687 holiday lettings
  • Norman Rockwell Museum: 681 holiday lettings
  • Naumkeag: 670 holiday lettings

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

Can I rent Houses in Stockbridge?

Yes, of course. Vrbo UK offers 394 Houses in Stockbridge. Our other popular types of Stockbridge holiday rentals include:

  • Cottages: 50 self catering accommodations
  • Cabins: 59 self catering accommodations
  • Flats: 37 self catering accommodations

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

Can I find a holiday accommodation with pool in Stockbridge?

Yes, you can select your preferred holiday accommodation with pool among our 72 holiday homes with pool available in Stockbridge. Please use our search bar to access the selection of holiday rentals available.