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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.

Greek Revival Farmhouse - Stockbridge, MA
9.9 129 reviews

Greek Revival Farmhouse

apartment, Stockbridge
This Stockbridge apartment is located just a short walk from the Norman Rockwell Museum and Chesterwood, offering easy access to two of the town's most popular attractions. The property enjoys excellent guest, location, and cleanliness ratings.
The apartment features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, parking, and internet access, along with a vintage modern design and hardwood floors throughout.
Historic Retreat - Stockbridge, MA
9.7 61 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.
Taggart River House: Modern Luxury Meets Nature: Stunning River Views, Sleeps 10 - Stockbridge, MA
9.8 16 reviews

Taggart River House: Modern Luxury Meets Nature: Stunning River Views, Sleeps 10

apartment, Stockbridge
This Stockbridge farm stay, a luxurious guest house near the Housatonic River, is two blocks from downtown Stockbridge and the Red Lion Inn, and within two miles of Tanglewood, the Norman Rockwell Museum, Chesterwood, and the Berkshire Botanical Garden.
The 4,500-square-foot property boasts five bedrooms, five and a half bathrooms, and accommodates up to ten guests, featuring a spacious open floor plan, modern amenities, and a terrace overlooking the river.
Hearth House  Prime Location! - Stockbridge, MA
9.4 7 reviews

Hearth House Prime Location!

apartment, Stockbridge
This Stockbridge apartment is located a short drive from the Norman Rockwell Museum, Tanglewood, and Main Street.
This 3-bedroom, 2.5-bathroom rental accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, sauna, and parking, with an outdoor yard and patio for relaxation.

Best Stockbridge, MA vacation rentals with air conditioning

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.
Berkshire Mountain Retreat - Stockbridge, MA
9.9 52 reviews

Berkshire Mountain Retreat

studio, Richmond
This studio is located in tranquil Richmond, offering doorstep access to miles of trails, and a short drive from renowned Berkshire attractions. With excellent user, location, and cleanliness ratings, this studio is a top choice for travelers.
The studio features a private entrance and patio with a grill and lounge chairs, a kitchen with a fridge, freezer, and microwave oven, air conditioning, and access to an in-ground pool during summer months. It accommodates up to 2 guests in 1 bedroom and 1 bathroom. Guests can enjoy hiking, biking, fishing, boating, swimming, shopping, and dining nearby.
Beautiful Berkshires 1-br Apartment - Stockbridge, MA
9.7 30 reviews

Beautiful Berkshires 1-br Apartment

apartment, Lee
This one-bedroom Lee, Massachusetts apartment offers easy access to Berkshire attractions.
The unit features a queen bed, full-size pull-out sofa, fully equipped kitchen, air conditioning, and parking, comfortably sleeping four guests.
Home Away From Home: Minutes To Tanglewood. - Stockbridge, MA
9.9 58 reviews

Home Away From Home: Minutes To Tanglewood.

apartment, Lenox
This Lenox house rental is minutes from downtown Lenox and Tanglewood, offering easy access to shops, restaurants, and the renowned music venue.
The three-bedroom, two-bathroom home sleeps seven guests comfortably and features a modern kitchen with stainless steel appliances, a private backyard, and parking for six cars.

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.

Lake View Berkshires Retreat - Private & Minutes To Lenox - Stockbridge, MA
10 31 reviews

Lake View Berkshires Retreat - Private & Minutes To Lenox

apartment, Lee
This Lee, Massachusetts lakeside home is located within two miles of the Berkshire Mountain Country Store, Housatonic River, Greenock Country Club, Wyndhurst Golf & Club, and the Animagic Museum of Animation.
This 3160-square-foot vacation rental boasts five bedrooms, four bathrooms, sleeps fourteen guests, and features a fully equipped kitchen, Jacuzzi, spa, tennis court, and a terrace overlooking the lake.
The Belden House - Walk To Tanglewood ! - Stockbridge, MA
10 2 reviews

The Belden House - Walk To Tanglewood !

apartment, Lenox
This historic 1881 Belden House, a National Historic Register landmark, offers a unique step back in time in Lenox, situated on 15 acres and a short walk to Tanglewood, 3 minutes from downtown Lenox and Stockbridge Bowl, and close to The Mount and Norman Rockwell Museum.
This 3800 square foot estate accommodates up to 10 guests with 6 bedrooms and 3 bathrooms, featuring a chef's kitchen with a Viking stove, a music room with a Steinway grand piano, a yoga and meditation room, a dedicated home office with high-speed Wi-Fi, a covered porch with rockers, and an outdoor dining area.
Stylish Mid-century Modern Berkshires Cape - Stockbridge, MA
9.9 145 reviews

Stylish Mid-century Modern Berkshires Cape

apartment, Lee
This 4-bedroom vacation home on a lake in Lee offers scenic views and is within walking distance of Greenock Country Club, Lee Library, and Animagic Museum of Animation. It has excellent user, location, and cleanliness ratings.
The house has a fully equipped kitchen, three bathrooms, a washing machine, a balcony, a smart TV, and free WiFi. It is pet-friendly, family-friendly, and has air conditioning, a terrace, a garden, and parking. It accommodates up to 8 guests and has a check-out time of 11:00 AM.
St Anne`s Manor | Walk To Downtown!  Sleeps 8 - Stockbridge, MA
10 127 reviews

St Anne`s Manor | Walk To Downtown! Sleeps 8

apartment, Lenox
This five-bedroom, three-bathroom Victorian home in downtown Lenox, Massachusetts, is a three-block walk from the bus station and within walking distance of numerous restaurants and shops.
This spacious rental boasts a well-equipped eat-in kitchen, a private backyard with a terrace and gas grill, and parking for three cars (shared driveway, plus street parking April 1st-November 1st), comfortably accommodating larger groups near Kennedy Park, Ventfort Hall, The Mount, and Arrowhead.

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.

Cozy Riverside Berkshires Retreat - Stockbridge, MA
9.6 23 reviews

Cozy Riverside Berkshires Retreat

apartment, Great Barrington
This riverfront duplex in Great Barrington offers convenient access to downtown, Chesterwood, and the Mahaiwe Performing Arts Center, with outdoor cats on the property.
This 3-bedroom, 1-bathroom apartment accommodates up to 8 guests and features a full kitchen with a microwave, spa, parking, and internet, making it suitable for events and outdoor activities like skiing and sledding.
Historic Family Retreat On The At & Housatonic! - Stockbridge, MA
No reviews

Historic Family Retreat On The At & Housatonic!

apartment, Lee
This historic 1815 farmhouse apartment in South Lee is located along the Appalachian Trail, 2 miles from Stockbridge and 3 miles from downtown Lee, offering proximity to Ski Butternut (10 miles), Bousquet Mountain (12 miles), and Goose Pond Reservation & October Mountain State Forest (6 miles).
This 1500 square foot dwelling accommodates up to 5 guests with 3 bedrooms and 2 bathrooms, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, a washer/dryer, and parking, with mountain and river views available from the shared yard.
Modern Chalet Near Tanglewood & Downtown Lenox - Stockbridge, MA
9.8 45 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

chalet, Lenox
This modern A-frame house is located in Lenox, within walking distance of Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor activities, and wellness retreats. The property has received excellent ratings for user experience, location, and cleanliness.
The house has a split-level design that can accommodate up to 6 guests and features a dedicated lower floor for children and elderly members, while the upper mezzanine provides privacy for adults. This family-friendly retreat offers a fully equipped kitchen, laundry facilities, a private garden, ample parking, and a basement with a ping pong table for entertainment.
Comfortable Elegance On Secluded Property In Lenox - Stockbridge, MA
10 96 reviews

Comfortable Elegance On Secluded Property In Lenox

apartment, Lenox
This five-bedroom home is located in Lenox, a short walk from the town center and two miles from Tanglewood, offering a peaceful retreat in a prime location. The apartment has received excellent ratings for user experience, location, and cleanliness.
This 2600 square foot home comfortably accommodates nine guests. Amenities include a fully equipped kitchen, a Jacuzzi, a garden, and parking, along with access to a spa and internet.

Best Stockbridge, MA vacation rentals with parking

The Blue House On The Bend - Stockbridge, MA
10 79 reviews

The Blue House On The Bend

apartment, 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
Exceptional Stockbridge Retreat - Stockbridge, MA
9.8 24 reviews

Exceptional Stockbridge Retreat

apartment, Stockbridge
Downtown Housatonic House 10 Miles To Tangelwood - Stockbridge, MA
9.8 10 reviews

Downtown Housatonic House 10 Miles To Tangelwood

apartment, Great Barrington

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.

Hawthorne House - Stockbridge, MA
10 2 reviews

Hawthorne House

apartment, Stockbridge

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.

Spacious 4br Central-berkshires Home With Pool! - Stockbridge, MA
10 3 reviews

Spacious 4br Central-berkshires Home With Pool!

apartment, Lee
Hike, Fish & Ski: Riverside Barn Loft In Lee - Stockbridge, MA
No reviews

Hike, Fish & Ski: Riverside Barn Loft In Lee

studio, Lee
Beautiful House In The Woods: Huge Yard, Hot Tub - Stockbridge, MA
10 10 reviews

Beautiful House In The Woods: Huge Yard, Hot Tub

apartment, Great Barrington
Fall Weekends And Ski Season Is Here! - Stockbridge, MA
10 1 review

Fall Weekends And Ski Season Is Here!

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.

The Ponds At Foxhollow - Stockbridge, MA
8.0 330 reviews

The Ponds At Foxhollow

resort, Lee
Condo ∙ 2 Bedrooms ∙ 6 Guests - Stockbridge, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox
Peaceful 1br Condo With Pond View - Stockbridge, MA
8.0 2 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox
The Summerwood Hideout | Mins To Downtown!  Pool - Stockbridge, MA
9.0 4 reviews

The Summerwood Hideout | Mins To Downtown! Pool

apartment, Great Barrington

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.

Beautiful House In The Woods, Huge Yard, Hot Tub - Stockbridge, MA
10 1 review

Beautiful House In The Woods, Huge Yard, Hot Tub

house, Great Barrington