Stockbridge vacation rentals
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The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
Top rated rentals - Stockbridge
Photo gallery for Clean & Modern space with a mix of original warmth and charming renovation.
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- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
The historic city of Stockbridge awaits you
Enjoy the area's museums, history and architecture and make a vacation rental your home during your stay in Stockbridge. 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 and around Stockbridge
Are you looking for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Stockbridge a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:
- Wyndhurst Golf & Club (4.7 mi / 7.6 km)
- Ski Butternut (7.2 mi / 11.6 km)
- Bousquet Ski Area (9.1 mi / 14.6 km)
- Catamount Ski Area (11.6 mi / 18.7 km)
- Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)
- Kennedy Park (6.8 mi / 10.9 km)
Exploring the natural features in Stockbridge
Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Stockbridge. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:
- Naumkeag Museum (0.3 mi / 0.4 km)
- Berkshire Botanical Garden (1.2 mi / 2 km)
- The Mount (3.8 mi / 6.2 km)
- Housatonic River Walk (6.6 mi / 10.6 km)
- Goose Pond Reservation (6.8 mi / 10.9 km)
- October Mountain State Forest (8.9 mi / 14.3 km)
Transportation options to and around Stockbridge
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.6 mi (15.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away.