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Stockbridge, Massachusetts, United States of America

Stockbridge vacation rentals

We found 479 vacation rentals — enter your dates for availability

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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Find spaces that suit your style

Houses

View 389 Houses

Cottages

View 49 Cottages

Cabins

View 56 Cabins

Condos/Apartments

View 39 Condos/Apartments

Studios

View 29 Studios

Bungalows

View 49 Bungalows

Find the best place to stay — Stockbridge

Modern Cottage in the heart of the Berkshires with new exterior flex space!

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
C$ 447 avg/night
(45)

Light-filled Berkshires country home

Sleeps 6 · 4 Bedrooms · 2 Bathrooms
C$ 314 avg/night

Stockbridge Cottage Minutes From Downtown Lenox

Sleeps 7 · 3 Bedrooms · 1 Bathroom
C$ 391 avg/night

General Williams Estate House Lenox/stockbridge

Sleeps 16 · 6 Bedrooms · 5 Bathrooms
C$ 1,068 avg/night
(72)

Stockbridge Bowl Lake Community

Sleeps 7 · 2 Bedrooms · 1 Bathroom
C$ 491 avg/night
(1)

A Grand Estate in Historic Stockbridge

Sleeps 12 · 6 Bedrooms · 6 Bathrooms
C$ 1,243 avg/night
(53)

Search 479 vacation rentals

Top rated rentals — Stockbridge
Stayed Jul. 2021

Stockbridge

My family and I relaxed at this house . Our group of 8 was comfortable in the Living room watching TV ,cooking and eating in the kitchen. Everyone had enough space. The pool was clean and we used it as much as possible. A few minor issues were taken ...

patricia o.
patricia o.
Stayed Jul. 2021

Accurate description, great location

Central to Stockbridge, Great Barrington, Lenox, Pittsfield, house is clean and spacious, with a well appointed kitchen. Lawn large and flat- great for outdoor games, nice porch out back, Pool was fine, fairly basic and unheated. Stockbridge bowl bea...

Pamela P.
Pamela P.
Stayed Jul. 2021

Berkshires paradise

This house was the perfect home base to explore the best of what the Berkshires has to offer--Tanglewood, Shakespeare and company, the Mount, the Clark, Mass MoCA, and great hiking. The space really felt like home, with a wonderful kitchen and dining...

Anna S.
Anna S.
Stayed Jul. 2021

Terrific house in the Berkshires

Wonderful small house nestled in the woods close to Lenox, Tanglewood, Stockbridge and all else in the Berkshires. A quick walk to the Stockbridge public beach and a beautiful swim. The house is very cute, and has absolutely everything one would need...

Edward A.
Edward A.
Stayed Jun. 2021

Beautiful property

What a fantastic find! This house and property are beautiful. Plenty of areas both inside and out for gathering, but lots of privacy for individuals with the large bedrooms and ensuite baths. Fully equipped kitchen. The porch, pool, large lawns and f...

Marjorie G.
Marjorie G.
Stayed Jun. 2021

Such an amazing place!

My husband and I stayed at the Taggart House with some friends and family for our wedding weekend and I was amazed at how perfect it was. There was more than enough space to entertain, the bedrooms were perfect and it made our weekend extra special. ...

Victoria D.
Victoria D.
Stayed Jun. 2021

Wonderful place

Five of us had a wonderful time at this house, which was immaculately clean, beautifully furnished, comfortable, and stocked with everything you could possibly need. Communication with the host before, during, and after our stay was quick and helpful...

Nancy G.
Nancy G.
Stayed Apr. 2021

A Beautiful Property

The house and grounds are really beautiful. There is a ton to do just on the property itself - with exploring the woods, the river, and yard. The house was spacious and well-equipped. The house is centrally located - with many major Berkshires towns ...

Sandy L.
Sandy L.

Boston, MA, USA

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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.

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