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Stockbridge, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Stockbridge, MA

Discover Family-Friendly Vacation Rentals in Stockbridge, MA

Make family travel to Stockbridge, MA seamless with spacious vacation rentals located just minutes from top city attractions.

Large Country Farmhouse In The Berkshires. - Stockbridge, MA
9.5 12 reviews
Stockbridge, MA
06/23 – 06/28
$856/nighttotal: $4280 (5 )

Large Country Farmhouse In The Berkshires.

1 2
apartment , Lee
This farmhouse is located in Lee, a short distance from town, restaurants, and grocery stores, offering easy access to amenities and local attractions. The property is highly rated by guests, with excellent scores for user experience, location, and cleanliness.
This spacious farmhouse can accommodate up to 9 guests, perfect for families or groups seeking a relaxing getaway. Amenities include a fully equipped kitchen, air conditioning, a private garden, and parking, as well as outdoor activities like fishing, hiking, and horseback riding.
Quiet, 3 Bedroom, One Story Home On 17 Acres. - Stockbridge, MA
10 1 review
Stockbridge, MA
06/23 – 06/28
$427/nighttotal: $2135 (5 )

Quiet, 3 Bedroom, One Story Home On 17 Acres.

1 2
apartment , West Stockbridge
This three-bedroom ranch-style house is located on 17 acres in the Berkshires, a 10-minute drive from Lenox and Great Barrington, offering seclusion and easy access to Berkshire attractions.
This West Stockbridge home sleeps eight guests and features a fully equipped kitchen with dishwasher, two bathrooms (one newly renovated), air conditioning, a garden, parking, and outdoor amenities including a deck and fire pit.
Private Modern Living On 120 Secluded Acres - Stockbridge, MA
9.7 41 reviews
Stockbridge, MA
06/23 – 06/28
$6008/nighttotal: $30040 (5 )

Private Modern Living On 120 Secluded Acres

9 2
house , Great Barrington
This 10-bedroom house, located on a mountain slope in the Berkshires, is just a 15-minute drive from Butternut and Catamount ski resorts, offering easy access to winter activities. The property has received excellent ratings for user experience, location, and cleanliness.
The house is ideal for large groups or families, with a main house, a guest house, and a spacious barn with a sleeping loft, kitchen, and amenities. The estate offers a variety of amenities, including a private pool, hot tub, hiking trails, a chef's kitchen, and a fire pit, perfect for relaxation and entertainment.
Dream Vacation - Stockbridge, MA
9.6 52 reviews
Stockbridge, MA
06/23 – 06/28
$388/nighttotal: $1940 (5 )

Dream Vacation

2 2
apartment , Lee
This Lee, Massachusetts rental is conveniently located near the Premium Outlets, Tanglewood, and Jacob's Pillow, offering easy access to Berkshire attractions.
The two-bedroom, two-bathroom apartment sleeps six, features a fully equipped kitchen with dishwasher, and includes amenities such as a swimming pool, jacuzzi, fitness center, and parking; summer weekly rentals and negotiable February weekday rates are available.

Best Stockbridge, MA vacation rentals with parking

Osceola Lodge - Stockbridge, MA
10 1 review
Stockbridge, MA
06/23 – 06/28
$2774/nighttotal: $13870 (5 )

Osceola Lodge

1 2
apartment , Lenox
This Lenox apartment is located a short walk from shops, restaurants, and attractions like Tanglewood and Shakespeare & Company, providing a convenient base for exploring the area. The apartment is a completely renovated 1889 mansion, offering spacious accommodation for up to 17 guests in 10 bedrooms and 9.5 bathrooms. The property features a heated indoor and outdoor pool, a spa tub, an 80-foot covered porch overlooking the pool and gazebo, parking for 8 vehicles, a bocce court, a pergola, a full house sound system, a 60-inch UHD TV, a backyard grill, 8 fireplaces, and a beautiful setting to soak in the surroundings.

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.

Destinations nearby

Top Vacation Rentals with Balconies in Stockbridge, MA

Start your morning right with a vacation rental in Stockbridge, MA featuring a private balcony and stunning views.

Mid- Century Modern Getaway - Stockbridge, MA
10 11 reviews
Stockbridge, MA
06/23 – 06/28
$953/nighttotal: $4765 (5 )

Mid- Century Modern Getaway

1 2
apartment , Stockbridge
This mid-century modern house in Lenox, Massachusetts, is less than a mile from Tanglewood, downtown Lenox, and Stockbridge Bowl, offering easy access to hiking trails, Kripalu Center for Yoga & Health, and Mount Greylock.
The three-bedroom, two-bathroom rental boasts a fully equipped kitchen, a private garden, six acres of wooded land leading to Lilly Pond, garage parking, and a smart lock, comfortably accommodating up to six guests.

Find the Best Dog-Friendly Vacation Rentals in Stockbridge, MA

Discover pet-friendly vacation rentals in Stockbridge, MA that prioritize comfort for both you and your dog.

Luxurious Family Home- Central Berkshire Location - Stockbridge, MA
10 2 reviews
Stockbridge, MA
06/23 – 06/28
$1214/nighttotal: $6070 (5 )

Luxurious Family Home- Central Berkshire Location

4 2
apartment , Richmond
This Richmond vacation rental is located just 3.2 miles from Tanglewood, a renowned music venue, and is close to other Berkshire attractions, making it a great base for exploring the region. It has earned excellent ratings for location, cleanliness, and overall user experience.
This spacious home has 4 bedrooms and 4 bathrooms, comfortably accommodating up to 10 guests. The property offers a screened-in porch with a dining table, seating areas, and a calming water fountain, perfect for enjoying the outdoors.
Quiet, 3 Bedroom, One Story Home On 17 Acres. - Stockbridge, MA
10 1 review
Stockbridge, MA
06/23 – 06/28
$427/nighttotal: $2135 (5 )

Quiet, 3 Bedroom, One Story Home On 17 Acres.

1 2
apartment , West Stockbridge
This three-bedroom ranch-style house is located on 17 acres in the Berkshires, a 10-minute drive from Lenox and Great Barrington, offering seclusion and easy access to Berkshire attractions.
This West Stockbridge home sleeps eight guests and features a fully equipped kitchen with dishwasher, two bathrooms (one newly renovated), air conditioning, a garden, parking, and outdoor amenities including a deck and fire pit.
Private Modern Living On 120 Secluded Acres - Stockbridge, MA
9.7 41 reviews
Stockbridge, MA
06/23 – 06/28
$6008/nighttotal: $30040 (5 )

Private Modern Living On 120 Secluded Acres

9 2
house , Great Barrington
This 10-bedroom house, located on a mountain slope in the Berkshires, is just a 15-minute drive from Butternut and Catamount ski resorts, offering easy access to winter activities. The property has received excellent ratings for user experience, location, and cleanliness.
The house is ideal for large groups or families, with a main house, a guest house, and a spacious barn with a sleeping loft, kitchen, and amenities. The estate offers a variety of amenities, including a private pool, hot tub, hiking trails, a chef's kitchen, and a fire pit, perfect for relaxation and entertainment.
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