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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.

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.
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.
Quaint & Cozy Loft - Stockbridge, MA
10 3 reviews

Quaint & Cozy Loft

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.

Best Stockbridge, MA vacation rentals with air conditioning

Wooded Cottage - Minutes From Lenox Village - Stockbridge, MA
9.9 184 reviews

Wooded Cottage - Minutes From Lenox Village

apartment, Lenox
This renovated cottage is located in Lenox, just a short walk from downtown and next to the historic Ventfort Hall. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
The two-bedroom cottage comfortably accommodates four guests and features a spacious dining room with access to a backyard patio. The fully equipped kitchen includes a fridge, microwave, and dishwasher, and the property offers amenities like air conditioning, a garden, and parking.
The Birds Nest - Stockbridge, MA
10 6 reviews

The Birds Nest

apartment, Lenox
This three-bedroom, three-bathroom Lenox apartment offers convenient downtown access to shops, restaurants, Tanglewood, and Shakespeare & Company.
The newly renovated rental sleeps six, features a fully equipped kitchen, air conditioning, parking, and is near pickleball and tennis courts.
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.
Justice's Birthplace: King Bed, Hearths, Gardens - Stockbridge, MA
9.7 85 reviews

Justice's Birthplace: King Bed, Hearths, Gardens

house, Lee
This charming farmhouse is located in Stockbridge, just a short distance from the town center and within easy reach of numerous attractions like The Mount, the Norman Rockwell Museum, and the Lee Premium Outlets. The house has received excellent ratings for its location, cleanliness, and overall experience.
The first-floor apartment offers a private entrance, porch, and gardens, comfortably accommodating up to four guests. Enjoy modern appliances, separate utilities, and a convenient location near ski resorts and cultural landmarks.

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.

Lakefront, Kayaks Included, Come Unwind In Lenox! - Stockbridge, MA
9.0 2 reviews

Lakefront, Kayaks Included, Come Unwind In Lenox!

apartment, Lenox
This newly renovated lakefront residence is located on Laurel Lake in Lenox, offering direct lakefront access and is within walking distance to The Mount (Edith Wharton's Home) and Shakespeare & Company, and a short drive to Tanglewood.
This 2150 square foot home features 4 bedrooms and 3 bathrooms, accommodating up to 10 guests with amenities including a chef's kitchen, wood-burning fireplace, enclosed 3-season porch with a foosball table, and a private dock for water activities.
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.
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.
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.

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.

Classic Tanglewood Retreat - Stockbridge, MA
10 9 reviews

Classic Tanglewood Retreat

apartment, Stockbridge
This Stockbridge vacation home, minutes from Berkshire attractions like Tanglewood, offers easy access to skiing and shopping.
The three-bedroom, two-bathroom house, accommodating up to nine guests, features a fully equipped kitchen, air conditioning, parking, a separate cottage, and outdoor amenities including cornhole, a frisbee, and a yard swing on nearly four acres.
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.
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.
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.

Best Stockbridge, MA vacation rentals with parking

Bella Rena Guesthouse - Stockbridge, MA
10 37 reviews

Bella Rena Guesthouse

house, Lenox
Hawthorne House - Stockbridge, MA
10 2 reviews

Hawthorne House

apartment, Stockbridge
Rustic Modern Retreat - Stockbridge, MA
9.8 72 reviews

Rustic Modern Retreat

apartment, West Stockbridge
Guest House In Stockbridge 3 Miles To Tanglewood - Stockbridge, MA
9.5 109 reviews

Guest House In Stockbridge 3 Miles To Tanglewood

house, Stockbridge

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.

Beautiful Berkshires 1-br Apartment - Stockbridge, MA
9.7 30 reviews

Beautiful Berkshires 1-br Apartment

apartment, Lee

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.

Light-filled Carpenter's Cottage - Stockbridge, MA
10 5 reviews

Light-filled Carpenter's Cottage

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

Fall Weekends And Ski Season Is Here!

apartment, Stockbridge
Riverhouse On Rising Pond - Stockbridge, MA
9.8 198 reviews

Riverhouse On 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.

Peaceful 1br Condo With Pond View - Stockbridge, MA
9.5 13 reviews

Peaceful 1br Condo With Pond View

apartment, Lee
Great Place|2 Bd|kitchen| Pool - Stockbridge, MA
9.6 18 reviews

Great Place|2 Bd|kitchen| Pool

resort, 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.

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

New! Berkshire Flat Overlooking Rising Pond!

apartment, Great Barrington
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