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Stockbridge, MA hotels
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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.
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.
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.
Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests - Stockbridge, MA
8.6 12 reviews
Stockbridge, MA
06/23 – 06/28
$632/nighttotal: $3160 (5 )

Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests

4 2
apartment , West Stockbridge
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.

Frequently Asked Questions about hotels in Stockbridge, MA

  • What amenities can travelers expect in hotel rooms in Stockbridge, MA?

    Most hotels in Stockbridge offer standard amenities like comfortable beds, private bathrooms, and Wi-Fi. Some hotels also have amenities like swimming pools, fitness centers, and on-site restaurants. You might even find a cozy fireplace in your room at some of the more charming inns.
  • What are the best hotels with a swimming pool in Stockbridge, MA?

    The Red Lion Inn, Wheatleigh and The Inn At Stockbridge are among the best hotels with a swimming pool in Stockbridge, MA.

  • When is the best time to book a hotel in Stockbridge, MA?

    The best time to book a hotel in Stockbridge is during the shoulder seasons, like spring and fall. You'll find lower rates and fewer crowds, making it a great time to explore the area.
  • What are the best luxury hotels in Stockbridge, MA?

    The Red Lion Inn and Wheatleigh are among the best luxury hotels in Stockbridge, MA.

  • What are some pet-friendly activities in and around Stockbridge, MA?

    Stockbridge is a great place to bring your furry friend! Many of the hiking trails in the Berkshires are dog-friendly, and you can often find dog-friendly patios at local restaurants. The Stockbridge Bowl is also a great place to let your dog run free.
  • What are the best family friendly hotels in Stockbridge, MA?

    The best family friendly hotels in Stockbridge, MA are The Red Lion Inn, Stockbridge Home 2 Blocks From Red Lion Inn and Wheatleigh.

  • Which towns or cities worth a visit near Stockbridge, MA?

    There are so many charming towns to explore near Stockbridge! Head north to Lenox, known for its beautiful scenery and the Tanglewood Music Center. Or visit Great Barrington, a vibrant town with a bustling arts scene and delicious restaurants.
  • What are the best pet friendly hotels in Stockbridge, MA?

    The best pet friendly hotels in Stockbridge, MA are The Red Lion Inn, Wheatleigh and The Inn At Stockbridge.

  • What are the best hotels with jacuzzi in Stockbridge, MA?

    The Red Lion Inn is the best hotel with a jacuzzi in Stockbridge, MA.

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