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 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 2020 accommodation listings offer a large selection of 450 holiday lettings around Stockbridge. From 50 cabins to 32 flats & apartments, 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.

Can I rent a mountain-view property in Stockbridge?

Nestle yourself and your clan high up in the mountains and get set for magnificent sunrises, otherworldly stargazing and loads of fresh air. HomeAway has no less than 123 alpine getaway rentals available. Alternatively, you may be searching for something else. HomeAway has oodles of options, including:

  • 114 rural holiday accommodation options.
  • 62 village holiday accommodation options.
  • 41 lake-view holiday accommodation options.

Can I rent a house in Stockbridge?

If you want to live like a local and love a bit of extra space and privacy, renting a whole house is the way to go. There are 255 houses listed on HomeAway. Prices begin at £65 a night. Or perhaps you'd rather choose one of the area's other popular self-catering accommodation options, such as:

  • Cottage: 24 self-catering accommodation options. Prices start from £77 per night.
  • Hotel: 19 self-catering accommodation options. Prices start from £84 per night.
  • Apartment: 19 self-catering accommodation options. Prices start from £96 per night.

Can I stay in Stockbridge in a large group?

It can be tricky finding time to unwind with your nearest and dearest. A holiday is an ideal way to reunite and unwind. If you were planning to stay under the same roof, HomeAway has options. 61 house holiday rentals are ready to be booked. Currently, they're the most popular choice here for sizeable groups. If you're planning on travelling in a big group, the properties for rent that are suitable for you include:

  • If yours is a crew of 6, we have 172 properties just right for that size. Stay a night from just £65.
  • Need somewhere for 8 guests? We have 136 that will serve you well. Prices begin at just £72 per night.
  • Trying to find rental properties suitable for 10 people? You'll be happy to discover we have 108 that will fit the bill. You can grab one for as little as £115 per night.

You and all your buddies will be well catered to when you plan your Stockbridge holiday with us!

Where are the cheapest holiday rentals in Stockbridge?

There are friends, there is family and then there are friends that become family. Make new memories with your nearest and dearest and organise a value-for-money holiday with HomeAway. Taconic is a terrific area to look at if you want to keep a handle on your budget. HomeAway has 4 holiday rentals, and the average price is an agreeable £114 per night. Sherwood Forest is another place to check out. We've got 11 and the average price is around £194 a night.