Holiday Rentals in Stockbridge, MA

115 available vacation rental offers

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Stockbridge, MA holiday rentals
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Stockbridge, MA Holiday rentals: no available offers. Here are other great options for your stay!

Rabbit Run In The Heart Of Stockbridge Village - Stockbridge, MA
9.8 116 reviews
Stockbridge, MA
14/10 – 21/10
342 €/nighttotal: 2394 € (7 )

Rabbit Run In The Heart Of Stockbridge Village

3 4
apartment , Stockbridge
This charming cottage is located in Stockbridge, just a short walk from the Red Lion Inn and within a 5-minute walk of hiking trails, a park, and tennis courts, offering easy access to both nature and entertainment. The property has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy the modern kitchen, high-speed internet, comfortable beds, and a sleeper couch, along with a beautiful fenced-in backyard with mountain views, a deck, grill, and fire pit.
Cabin Fever In Stockbridge - Stockbridge, MA
9.8 257 reviews
Stockbridge, MA
14/10 – 21/10
598 €/nighttotal: 4186 € (7 )

Cabin Fever In Stockbridge

1 4
apartment , Stockbridge
This charming cottage is located in a peaceful lake neighbourhood in Stockbridge, just 1.6 kilometres from the public beach at Stockbridge Bowl. It has received excellent ratings for its location, cleanliness, and overall experience.
The 84 square metre cottage comfortably sleeps six guests and features a spacious outdoor area with a sunny deck, a charming fieldstone fireplace, and a dedicated reading nook. Enjoy the modern amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, and parking.
The Hideaway On Main - Stockbridge, MA
10 6 reviews
Stockbridge, MA
14/10 – 21/10
322 €/nighttotal: 2254 € (7 )

The Hideaway On Main

1 4
apartment , Stockbridge
This Stockbridge cottage-style apartment is centrally located, steps from the town centre and its shops, restaurants and galleries.
The two-bedroom, one-bathroom flat sleeps four guests and features a fully equipped kitchen with high-end appliances, a private rear deck with gas grill, and a dedicated parking space.
Three Bedroom Duplex In Stockbridge On The River - Stockbridge, MA
10 53 reviews
Stockbridge, MA
14/10 – 21/10
322 €/nighttotal: 2254 € (7 )

Three Bedroom Duplex In Stockbridge On The River

3 4
apartment , Stockbridge
This three-bedroom duplex is situated just a short walk from Stockbridge's charming town centre, with its museums, restaurants, and hiking trails. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The property can comfortably accommodate up to six guests and features a spacious garden, a private riverfront area, and a fully equipped kitchen. Guests can enjoy the peace and quiet of the surrounding Berkshire Mountains, while also having access to a range of activities, including kayaking, fishing, and relaxing by the fire pit.

Frequently asked questions about holiday rentals in Stockbridge, MA

  • What are some interesting places to visit in or near Stockbridge, MA?

    Stockbridge is a charming town with plenty to see and do. You can visit the Norman Rockwell Museum, which showcases the iconic artist's work, or explore the grounds of the Naumkeag estate, a beautiful example of an early 20th-century country house. A short drive away is the vibrant city of Lenox, home to Tanglewood, the summer home of the Boston Symphony Orchestra.
  • What are the best Airbnb and holiday rentals in Stockbridge, MA?

  • Which walking or cycling routes are the best in Stockbridge, MA?

    Stockbridge is a great place to explore on foot or by bike. The Stockbridge Bowl Loop is a popular 5km walk or cycle around the lake. If you're looking for a longer ride, the scenic 25km Housatonic River Rail Trail is a great option, offering views of the river and surrounding countryside.
  • What are the most popular Airbnbs in Stockbridge, MA?

  • What sports or outdoor activites can visitors enjoy in and around Stockbridge, MA?

    Stockbridge offers a range of outdoor activities. You can go hiking in the Berkshires, kayaking on the Stockbridge Bowl, or play a round of golf at the Stockbridge Golf Club. For a more unique experience, try fly fishing on the Housatonic River.
  • What are the best holiday rentals with a pool in Stockbridge, MA?

  • What other towns or cities can be easily accessed from Stockbridge, MA?

    Stockbridge is well-positioned for exploring the Berkshires. You can easily reach the charming towns of Lenox, Great Barrington, and Lee, all within a 30-minute drive. For a larger city experience, Albany, New York is about a 2-hour drive.
  • What are the best rentals for families and kids in Stockbridge, MA?

  • What amenities are commonly available in vacation rentals in Stockbridge, MA?

    Vacation rentals in Stockbridge typically offer a range of amenities to make your stay comfortable. Most have fully equipped kitchens, laundry facilities, and comfortable living areas. Some might also include outdoor spaces like patios or decks, fireplaces, and hot tubs.
  • What are the best rentals or Airbnbs with a jacuzzi in Stockbridge, MA?

  • What time of year is best to rent a vacation rental Stockbridge, MA?

    The best time to visit Stockbridge depends on your preferences. Summer is popular for outdoor activities, while autumn offers stunning foliage. Spring and winter are quieter, with opportunities for skiing and snowshoeing.
  • What are the local dishes in Stockbridge, MA region?

    The Berkshires are known for their farm-to-table cuisine, so you'll find plenty of fresh, local ingredients in the restaurants. Try the Berkshire pork, which is renowned for its flavour, or sample some of the local cheeses and craft beers. The region also has a strong tradition of apple orchards, so you'll find many apple-based dishes on the menus.

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