Discover a selection of 446 vacation rentals in Stockbridge, MA 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 swimming pools and kitchens. Prices start at $280 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.
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 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, MA?

Our 2020 property listings offer a large selection of 446 vacation rentals around Stockbridge. From 298 house rentals to 50 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Stockbridge?

We all enjoy a room with a view. But if you're after scenery that'll leave you feeling like you're on cloud nine, you'll have to head for the hills. Vrbo has 123 alpine rentals available. Open to other ideas? Vrbo has oodles more options to take a look at, including:

  • 114 rural vacation rentals.
  • 62 village vacation rentals.
  • 41 lake-view vacation rentals.

Can I rent a house in Stockbridge?

If you want to live like a local and love having lots of room to move, renting an entire house is the way to go. There are 255 houses currently listed on Vrbo. Prices begin at $85 per night. Or maybe you'd rather go for one of the area's other lodging types, like:

  • Cottage: 24 vacation homes. Prices start from $100 per night.
  • Hotel: 19 vacation homes. Prices start from $109 per night.
  • Apartment: 19 vacation homes. Prices start from $125 per night.

Can I stay in Stockbridge in a large group?

Getting together with family can be tons of fun, especially when you're sleeping under the same roof somewhere new! If you're visiting with a large group, Vrbo can help. House vacation homes are the top choice here for large groups of guests. Our international database presently has 61 available. The rental properties that are suitable for large groups here include:

  • Are you searching for vacation homes that can sleep 6 guests? We have 172 that will be perfect. Prices start from $85 per night.
  • Looking for a place for 8 people? We have 136 that will suit. You can get one for as little as $93 a night.
  • Trying to find places for rent to suit 10 guests? You'll be thrilled to discover we have 108 that will fit the bill. You can secure one from just $150 a night.

So don't worry! When you book with us you can bring along your uncle, your cousins and all your friends to Stockbridge.

Where are the cheapest rentals in Stockbridge?

Friends are the family we choose for ourselves. Rejuvenate the bonds with the ones you hold dear and book a value-for-money escape with Vrbo. When it comes to getting your hands on an amazing deal, your first stop should be Taconic. Here, Vrbo has 4 rentals at an average price of $148 per night. Sherwood Forest is another good option. We have 11 rentals here, and the average price is around $253 per night.