Compare best Airbnb in Stockbridge, MA from 100+ providers!

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Stockbridge, MA vacation rentals
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Stockbridge, MA Vacation 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
10/14 – 10/21
$396/nighttotal: $2772 (7 )

Rabbit Run In The Heart Of Stockbridge Village

3 4
apartment , Stockbridge
This historic Stockbridge apartment with 3 bedrooms and 2 bathrooms is in a convenient location, steps from the Red Lion Inn. It is near hiking trails, a park, and tennis courts (within 5 minutes walking distance). It has an excellent user rating, location rating, and cleanliness rating.
The apartment has a private, fenced-in backyard with mountain views and outdoor seating, lake rights to Stockbridge Bowl, a Weber grill and Solo firepit for backyard relaxation, comfortable beds with high-end bedding, high-speed internet, and unique furniture from Glenn Close's estate sale. It allows pets and is family-friendly. It has air conditioning, a kitchen with a fridge, freezer, microwave oven, and dishwasher, a fitness center, parking, and a garden. It can accommodate up to 8 guests.
Berkshires Gem In Pvt Community - Stockbridge, MA
10 8 reviews
Stockbridge, MA
10/14 – 10/21
$466/nighttotal: $3262 (7 )

Berkshires Gem In Pvt Community

1 4
apartment , Stockbridge
This Stockbridge vacation home, located in the Beachwood community on Lake Mahkeenac, offers private beach access and is within a couple of miles of Lenox and Stockbridge attractions like Tanglewood and the Norman Rockwell Museum.
The three-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen, fireplace, screened porch, patio with grills, paddleboards, and board games, and provides air conditioning and heating.
Charming Berkshires Getaway - Stockbridge, MA
10 25 reviews
Stockbridge, MA
10/14 – 10/21
$361/nighttotal: $2527 (7 )

Charming Berkshires Getaway

1 4
apartment , Lee
This renovated 1910 farmhouse in Lee, Massachusetts, is a three-minute drive from Lee's main street shops and restaurants, providing easy access to Berkshires attractions.
This three-bedroom, two-bathroom house sleeps seven guests and features a kitchen with a fridge and microwave, air conditioning, a garden, parking, and excellent user ratings for location and cleanliness.
Meadowbrook Cottage - Stockbridge, MA
10 31 reviews
Stockbridge, MA
10/14 – 10/21
$283/nighttotal: $1981 (7 )

Meadowbrook Cottage

1 4
apartment , Lee
This charming cottage is located just minutes from popular Berkshire attractions like Stockbridge Center, Lee Premium Outlets, and Lenox Center, making it the perfect base for exploring the area. The surrounding foothills of October Mountain offer stunning meadow views and a peaceful, natural setting.
This cozy home features one bedroom with a queen-sized bed and a queen-sized pull-out sofa bed in the living room, comfortably accommodating up to four guests. Enjoy modern conveniences like a fully equipped kitchen with a coffee bar, quartz counters, and stainless steel appliances, a washer and dryer, air conditioning, and a private garden with an outdoor dining area and fire pit.

Frequently Asked Questions about vacation rentals in Stockbridge, MA

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

    Stockbridge is full of charm! You can visit the Norman Rockwell Museum, explore the grounds of the historic Naumkeag estate, or take a stroll through the beautiful Tanglewood Music Center. If you're looking for something a bit further out, you could head to the vibrant city of Lenox, just 10 miles away, or the charming town of Great Barrington, about 15 miles south.
  • What are the best Airbnb and vacation rentals in Stockbridge, MA?

    A Grand Property In Historic Stockbridge, Tranquil 3 Br Stockbridge House With Private Deck and Modern Studio With Views Of The Treetops are the most popular Airbnb and vacation rentals in Stockbridge, MA among travelers.

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

    The Stockbridge Bowl is a popular spot for both walking and cycling. It's a beautiful, scenic loop around the lake, perfect for a leisurely stroll or a more vigorous bike ride. If you're looking for something a bit more challenging, you could try the scenic route up to the top of Monument Mountain, offering breathtaking views of the 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 is a great place for outdoor enthusiasts. You can go hiking or biking in the Berkshires, kayaking or canoeing on the Stockbridge Bowl, or even go skiing or snowboarding at nearby Jiminy Peak Mountain Resort in the winter. There's something for everyone here, no matter the season.
  • What are the best vacation rentals with a pool in Stockbridge, MA?

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

    You can easily reach nearby towns like Lenox, Lee, and Great Barrington by car. If you're looking for a bigger city, you can drive to Albany, New York, which is about an hour and a half away, or to Springfield, Massachusetts, which is about 45 minutes away.
  • What are the best rentals for families and kids in Stockbridge, MA?

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

    Most vacation rentals in Stockbridge offer basic amenities like Wi-Fi, a fully equipped kitchen, and laundry facilities. Many also have fireplaces, outdoor spaces with grills, and even hot tubs. Some rentals are even pet-friendly, so you can bring your furry friend along.
  • 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 really depends on what you're looking for. If you enjoy the crisp fall air and vibrant foliage, September and October are great months. If you're looking for a more peaceful getaway, spring and early summer are lovely. And for winter sports enthusiasts, December through February is the perfect time to visit.

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