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

Find Vacation Rentals in Downtown of Stockbridge, MA

Choose a downtown Stockbridge, MA vacation rental for easy sightseeing. Compare the top centrally located properties and book your city stay with confidence.

Historic Retreat - Stockbridge, MA
9.7 59 reviews

Historic Retreat

apartment, Stockbridge
This Stockbridge studio apartment is situated above a coffee shop and art studio, minutes from Tanglewood and close to Naumkeag and the Edith Wharton Restoration.
The unit features a private bathroom, ample storage, and accommodates two guests, offering easy access to Stockbridge's cultural attractions and the historic Red Lion Inn.
Your Stockbridge Getaway - Stockbridge, MA
9.9 28 reviews

Your Stockbridge Getaway

apartment, Stockbridge
St. Joseph's Rectory is a historic accommodation located in the heart of Stockbridge, adjacent to St. Joseph's Church and the Divine Mercy Shrine. It offers a tranquil retreat with a private garden and exquisite interior, blending timeless elegance with modern comfort.
The rectory has 5 bedrooms, 2 bathrooms, and can accommodate up to 13 guests. It features a fully equipped kitchen, laundry facilities, and parking. Guests enjoy exclusive access to the entire house except for the attached garage. The rectory retains its original architectural features, offering a glimpse into Stockbridge's past.
Modern Barn In The Heart Of The Berkshires - Stockbridge, MA
9.8 174 reviews

Modern Barn In The Heart Of The Berkshires

house, Stockbridge
This unique and charming renovated 1940s dairy barn in Stockbridge offers a tranquil escape just minutes from Main Street, Tanglewood, and the Stockbridge Bowl. With excellent user, location, and cleanliness ratings, this house is a great choice for travelers visiting Stockbridge.
The house has 2 bedrooms, 1 bathroom, and can accommodate up to 4 guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and a large Roku TV for entertainment. Guests can also enjoy outdoor grilling and dining, and have the option to indulge in authentic home-cooked Indian meals prepared by the host.
Light-filled Carpenter's Cottage - Stockbridge, MA
10 5 reviews

Light-filled Carpenter's Cottage

apartment, Stockbridge
This Stockbridge cottage is situated on a south-facing hill with views of Monument Mountain, offering a private retreat just a short distance from family, with the highway's hum audible.
This pet-friendly apartment accommodates two guests and features a kitchen, air conditioning, one bathroom, a private deck with seating for six, and access to explore the surrounding woods and stream.

Best Stockbridge, MA vacation rentals with air conditioning

Fall Weekends And Ski Season Is Here! - Stockbridge, MA
9.6 11 reviews

Fall Weekends And Ski Season Is Here!

house, Stockbridge
This Stockbridge apartment is conveniently located just two miles from Tanglewood, less than five minutes from Stockbridge Town Beach, and five minutes from downtown Stockbridge. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom, two-bathroom home comfortably sleeps six guests. You’ll enjoy modern amenities like a fully equipped kitchen, laundry facilities, high-speed internet, and a cozy fireplace, along with outdoor spaces like a sun deck with a fire pit and a spacious backyard.
Hawthorne House - Stockbridge, MA
10 2 reviews

Hawthorne House

apartment, Stockbridge
This 3-bedroom, 2.5-bathroom apartment in Stockbridge, MA, offers central Berkshires access, situated a 10-minute drive from Tanglewood, downtown Lenox, Lee, and Pittsfield.
This pet-friendly rental includes two living areas, a full kitchen, laundry, a deck, a patio with a firepit, and parking for at least 4 cars, accommodating up to 7 guests.
Lakeside Estate 2 Homes For Family Gatherings - Stockbridge, MA
No reviews

Lakeside Estate 2 Homes For Family Gatherings

house, Lenox
This Lenox vacation home is located 1.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewood Musical Center, offering convenient access to local attractions.
This air-conditioned rental accommodates up to 18 guests with 1 bedroom and 5 bathrooms, featuring complimentary WiFi, a full kitchen, a garden, and private parking.
Cozy Berkshires Pied-à-terre - Stockbridge, MA
9.8 13 reviews

Cozy Berkshires Pied-à-terre

apartment, Lenox
This Lenox apartment rental is centrally located, minutes from Shakespeare & Company, Tanglewood, Miraval, and October Mountain State Forest, offering easy access to the Mass Pike.
The two-bedroom, one-bathroom unit sleeps five, features a fully equipped kitchen with dishwasher, in-unit laundry, a private porch and yard, and a Level 3 Ford EV charger; nearby attractions include Bousquet, Butternut, and Otis Ridge ski areas.

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.

Popular destinations

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.

Lakeside Estate: 2 Homes For Family Gatherings - Stockbridge, MA
10 1 review

Lakeside Estate: 2 Homes For Family Gatherings

apartment, Lenox
This exclusive lakeside estate in Lenox, Massachusetts, offers private lake access and is within walking distance of The Mount, Edith Wharton's Home, and a short drive to Tanglewood.
This spacious rental property features 8 bedrooms and 5 bathrooms, accommodating up to 18 guests with amenities including a chef's kitchen, internet, air conditioning, and year-round activities such as skiing at nearby Bousquet and Ski Butternut.
General Williams Estate House Lenox/stockbridge - Stockbridge, MA
9.8 120 reviews

General Williams Estate House Lenox/stockbridge

apartment, Stockbridge
This spacious Stockbridge estate, two miles from Stockbridge Center and five miles from Lenox Center, offers easy access to the Mass Pike and Berkshire attractions.
The 5,500-square-foot home boasts six bedrooms, six bathrooms, and accommodates up to sixteen guests, featuring two kitchens, a pool, a spa, and ample outdoor space perfect for family gatherings or group retreats.
Imagine Being Lakeside, Kayaks/fishing/ev Charger - Stockbridge, MA
9.6 23 reviews

Imagine Being Lakeside, Kayaks/fishing/ev Charger

apartment, Lenox
This Lenox vacation home is near the beach, a 15-minute walk from Wyndhurst Golf & Club and The Mount, and within 3 miles of Shakespeare & Company and Ventfort Hall Mansion.
This 1890-square-foot property boasts four bedrooms, two bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen, a terrace, a garden, parking, and a DVD player, perfect for families or groups exploring Lenox's attractions.
The Ponds At Foxhollow - Stockbridge, MA
8.0 332 reviews

The Ponds At Foxhollow

resort, Lee
The Ponds at Foxhollow By Capital Vacations is located in Lenox, Massachusetts, just 2.5 miles from the renowned Tanglewood music venue. The resort has received very good user ratings, with excellent ratings for its location and very good ratings for cleanliness.
The resort offers a variety of accommodations, including villas and apartments. Guests can enjoy a range of amenities, including indoor and outdoor pools, a fitness center, a sauna, and free bicycle rentals.

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.

Hip Stockbridge Cabin - A Stroll To The Lake - Stockbridge, MA
9.8 254 reviews

Hip Stockbridge Cabin - A Stroll To The Lake

cabin, Stockbridge
This Stockbridge cabin is located in a serene lake neighborhood with a charming bohemian interior, just steps away from the picturesque Stockbridge Bowl. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 900 square feet and can accommodate up to 6 guests. It features a cozy sleeping loft, a reading nook, and a fieldstone fireplace. The spacious yard, sunny deck, and outdoor amenities make it perfect for relaxation and outdoor entertainment.
Light Filled - Modern Rustic Home - Stockbridge, MA
10 5 reviews

Light Filled - Modern Rustic Home

apartment, Stockbridge
This Stockbridge apartment offers a private retreat on a quiet dead-end road, providing direct access to the natural beauty of the surrounding woods and stream.
This pet-friendly unit accommodates up to six guests with two bathrooms, a full kitchen, air conditioning, and internet, featuring an outdoor deck and yard ideal for relaxation and recreation.
Peaceful Stockbridge Cabin In The Woods - Stockbridge, MA
9.7 126 reviews

Peaceful Stockbridge Cabin In The Woods

apartment, Stockbridge
This secluded apartment in the Berkshire foothills is just a short drive from Stockbridge's renowned attractions. It boasts an excellent user rating and is praised for its cleanliness and location.
The apartment has two bathrooms and can accommodate up to eight guests. It features a cozy interior with a fireplace, a deck overlooking the woods, and newly upgraded mattresses. Guests can enjoy on-site amenities such as a ping pong room, a studio space, ample parking, and a private washer and dryer.
Condo ∙ 1 Bedroom ∙ 4 Guests - Stockbridge, MA
No reviews

Condo ∙ 1 Bedroom ∙ 4 Guests

apartment, Lenox
This Lenox, MA condo, located in the Ponds at Foxhollow development, is 4.3 miles from Tanglewood, 2.9 miles from The Mount, and 7.2 miles from the Norman Rockwell Museum.
The one-bedroom, two-bathroom apartment sleeps four, features a fully equipped kitchen, in-unit laundry, a fireplace, access to a pool, fitness center, and sauna, and is near numerous hiking trails.

Best Stockbridge, MA vacation rentals with parking

Riverhouse On Rising Pond - Stockbridge, MA
9.8 198 reviews

Riverhouse On Rising Pond

apartment, Great Barrington
Cozy Berkshire Cottage Style Apartment - Stockbridge, MA
9.5 131 reviews

Cozy Berkshire Cottage Style Apartment

apartment, Lee
The Birds Nest - Stockbridge, MA
10 6 reviews

The Birds Nest

apartment, Lenox
Charming Downtown Lenox Getaway At 30 Franklin - Stockbridge, MA
10 3 reviews

Charming Downtown Lenox Getaway At 30 Franklin

apartment, Lenox

Best 5-Star Vacation Rentals in Stockbridge, MA

Elevate your stay in a luxury vacation rental or Airbnb in Stockbridge, MA, featuring high-end finishes and a prime location.

Charming Downtown Lenox Getaway At 30 Franklin - Stockbridge, MA
10 3 reviews

Charming Downtown Lenox Getaway At 30 Franklin

apartment, Lenox

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.

Classic New England Home With A Swimming Pool - Stockbridge, MA
9.9 17 reviews

Classic New England Home With A Swimming Pool

apartment, Richmond
Fall Weekends And Ski Season Is Here! - Stockbridge, MA
No reviews

Fall Weekends And Ski Season Is Here!

apartment, Stockbridge
New! Berkshire Flat Overlooking Rising Pond! - Stockbridge, MA
No reviews

New! Berkshire Flat Overlooking Rising Pond!

apartment, Great Barrington
Meadow's Edge - Modern Retreat W/ In Law Suite - Stockbridge, MA
10 2 reviews

Meadow's Edge - Modern Retreat W/ In Law Suite

apartment, Stockbridge

Search Vacation Rentals with Swimming Pool in Stockbridge, MA

A vacation rental with a pool in Stockbridge, MA makes it easy to fit in a proper swim right in the heart of the city.

Great Place|2 Bd|kitchen| Pool - Stockbridge, MA
9.5 22 reviews

Great Place|2 Bd|kitchen| Pool

aparthotel, Lee
Peaceful 1br Condo With Pond View - Stockbridge, MA
8.8 3 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox

Top-Rated Vacation Rentals with a Hot Tub in Stockbridge, MA

Coming home to a private hot tub after a day of urban exploration completely transforms your Stockbridge, MA experience.

Classic Stockbridge Cottage - Stockbridge, MA
9.8 36 reviews

Classic Stockbridge Cottage

house, Stockbridge
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