Compare best Airbnb in Stockbridge, MA from 100+ providers!
115 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in 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.
This West Stockbridge vacation rental is located in the mountains, within a 3-mile radius of local attractions like Hoffman's Pottery and Chesterwood. It has received very good user ratings. This 3-bedroom, 3200 square foot home comfortably accommodates up to 6 guests. Enjoy the peaceful mountain setting, relax by the fireplace, and make use of the fully equipped kitchen, private patio, and outdoor barbecue.
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.
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.
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.
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.
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.
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.
Stockbridge, MA
06/23 – 06/28
$509/nighttotal: $2545 (5 )
Berkshires/lenox
1 2
apartment , Lenox
This Lenox apartment is situated in an 1840 Victorian home, a short distance from the Bousquet Ski Area and other attractions like Butternut. The charming Berkshires setting offers a peaceful retreat for travelers seeking a unique experience. This cozy, one-bedroom unit features a private entrance and fenced patio area. The apartment offers amenities including a full kitchen, a swimming pool, a garden, parking, and free laundry facilities, making it ideal for couples seeking a comfortable and convenient stay.
Stockbridge, MA
06/23 – 06/28
$2682/nighttotal: $13410 (5 )
Berkshire Serenity: Mountain, Field, Lake
5 2
apartment , Great Barrington
This 5-bedroom rental is located near Great Barrington, offering a peaceful escape surrounded by fields, woods, and a lake. The location allows for easy access to the town's shops, restaurants, and cultural attractions, as well as the Berkshires' hiking trails and scenic drives. This spacious rental accommodates up to 9 guests and features a fully equipped kitchen, a swimming pool, and parking. Enjoy amenities like internet access, a tranquil setting, and a peaceful atmosphere.
10 2 reviews
Stockbridge, MA
06/23 – 06/28
$444/nighttotal: $2220 (5 )
Quaint & Cozy Loft
1 2
apartment , Stockbridge
This Stockbridge loft apartment offers stunning views of Norman Rockwell's home and the village street, providing easy access to local attractions. The one-bedroom, one-bathroom unit features a galley kitchen, fireplace, hardwood floors, and accommodates two guests, perfect for exploring Stockbridge's historical sites and charming village.
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.
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.
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.
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.
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
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?
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.
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.
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.
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.
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.