Compare Vacation Rentals & Airbnb in Stockbridge, MA

This charming cottage is situated in the quintessential Berkshire village of Stockbridge, just a short walk from the Red Lion Inn and within a 5-minute walk of hiking trails, a park, and tennis courts. The property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
This 158 square metre property has three bedrooms, two bathrooms, and can accommodate up to eight guests. The cottage features a well-equipped kitchen, a comfortable living area, a fenced-in backyard with mountain views, and a range of amenities including a foosball table, dart board, yoga mats, a Weber grill, a Solo firepit, and lake rights to the Stockbridge Bowl.

This three-bedroom holiday home is located on 17 acres in the Berkshires, a 10-minute drive from Lenox and Great Barrington.
This family-friendly property accommodates up to eight guests and features air conditioning, a dishwasher, Wi-Fi, and a garden with a deck and fire pit, offering a secluded escape with excellent ratings for location, cleanliness, and user experience.

This charming cottage is located in a peaceful lake neighbourhood in Stockbridge, just 1.6 kilometres from the public beach at Stockbridge Bowl. It has received excellent ratings for its location, cleanliness, and overall experience.
The 84 square metre cottage comfortably sleeps six guests and features a spacious outdoor area with a sunny deck, a charming fieldstone fireplace, and a dedicated reading nook. Enjoy the modern amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, and parking.

This four-bedroom detached house in Stockbridge is situated a short distance from Stockbridge Bowl and Tanglewood, offering views of the surrounding forest and mountains.
This family-friendly property can accommodate up to ten guests and features a fully equipped kitchen, a wood-burning fireplace, and outdoor amenities including a barbecue and picnic area, with AvantStay's concierge services available.

This charming house is located in Stockbridge, just 2.3 kilometres from the Norman Rockwell Museum, 8.5 kilometres from Tanglewood Musical Center, and 9.2 kilometres from Tanglewood, offering a peaceful retreat in a picturesque setting. The property enjoys excellent ratings for cleanliness, location, and user experience.
The house spans 149 square metres and comfortably accommodates up to six guests in three bedrooms. The property offers a range of amenities, including a fully equipped kitchen, air conditioning, free Wi-Fi, a private deck, and a spa, making it ideal for a relaxing and enjoyable stay.

This holiday home is located just outside Stockbridge, a short drive from the Berkshire Botanical Garden (2.9 km) and Tanglewood Music Center (4.2 km), offering a peaceful and scenic setting for your stay. The property has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The spacious property spans 152 square metres and comfortably accommodates up to 7 guests in its 4 bedrooms and 2 bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden with barbecue facilities, a private patio, and a spa, making it perfect for relaxing and enjoying the beautiful surroundings.

This Lenoxshire cottage, two miles (3.2km) from Lenox town centre and a five-minute drive from its attractions, offers privacy amidst trees and proximity to local amenities.
The recently renovated (2022) property features two bedrooms, one bathroom, sleeps three, includes a fully equipped kitchen, a dedicated studio building, and a spacious deck and private garden.

This 1900 farmhouse is situated in the village of Stockbridge, just a short walk from restaurants, shops, and the Red Lion Inn, and a short drive from Tanglewood, the Norman Rockwell Museum, and the Berkshire Botanical Garden. It has been rated excellent by previous guests.
The farmhouse has two bedrooms, two bathrooms, and a floor area of 111 square metres, comfortably accommodating up to four guests. It provides a tranquil escape with a garden, terrace, and riverfront access, alongside a fully equipped kitchen, a baby grand Yamaha piano, and a cosy upstairs sitting room.

This Lenox holiday home, near the beach and a 2.4km walk from Wyndhurst Golf & Club and The Mount, offers easy access to local attractions including Shakespeare and Company and Ventfort Hall Mansion within 5km.
The 176 square metre property boasts four bedrooms, two bathrooms, sleeping up to ten guests, and features a fully equipped kitchen, private balcony, garden, parking, and internet access.

The Ponds at Foxhollow by Capital Vacations is located in Lenox, Massachusetts, just a short drive from Tanglewood and the Tanglewood Musical Center, making it a great choice for music lovers and those looking to explore the scenic Berkshires. The resort enjoys excellent location and cleanliness ratings, with guests consistently praising its comfortable and well-maintained accommodation.
Each apartment features a fully equipped kitchen and a dining and seating area with a TV, providing everything you need for a relaxing stay. Guests can enjoy a range of amenities, including a seasonal outdoor pool and hot tub, an indoor pool, sauna, fitness center, and tennis court, as well as free bicycle use, fishing, and canoeing opportunities.

This West Stockbridge holiday home is situated a 7-minute drive from Tanglewood Music Centre and a 6-minute drive from Hotchkiss Mobile Studio.
This five-bedroom, three-bathroom property offers a swimming pool, garden, terrace, hot tub, and Wi-Fi, making it ideal for families exploring local attractions and natural beauty spots.

This family-friendly holiday home is situated near the lake in Lee, within a mile of Greenock Country Club and the Housatonic River, and within two miles of the Animagic Museum of Animation and Lee Library. This property enjoys excellent user ratings, making it a popular choice for travellers visiting Lee.
The house has 5 bedrooms, 4 bathrooms, and a floor area of 260 square metres, comfortably accommodating up to 14 guests. Amenities include a fully equipped kitchen, a fireplace, a terrace, a garden, a fitness centre, and a spa, ensuring a comfortable and enjoyable stay.

This three-storey cabin, near Great Barrington, West Stockbridge, and Lenox, offers a secluded cul-de-sac location with waterfall views and is approximately 3.2km from Tanglewood and Kripalu.
The property features an open-loft design, sleeps up to six guests in three bedrooms and one bathroom, includes a well-equipped kitchen, a hot tub (available April-December), and provides Wi-Fi, parking, and accepts pets.

This family-friendly villa is situated in a peaceful rural setting in Lenox, just 1.6 km from Ventfort Hall Mansion and Gilded Age Museum, The Bookstore, and Shakespeare and Company. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious 1,394 square metre property offers 13 bedrooms and 13.5 bathrooms. Enjoy the convenience of a fully equipped kitchen, a fitness centre, a sauna, a tennis court, and a garden with barbecue facilities.

This modern A-frame cabin is located in Lenox, just a short walk from Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor recreation, and wellness activities. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cabin features a split-level mezzanine design, offering a blend of modern and rustic charm, and can accommodate up to six guests. Enjoy stunning views of the Berkshires from the open living room with triple-height ceilings, relax on the sun porch or deck, or unwind in the garden hammocks. The cabin also includes a fully equipped kitchen, a private garden, a ping pong table, and BBQ facilities available upon request.

This luxurious Lenox penthouse apartment, situated above Bistro Zinc in the town centre, offers convenient access to Lenox's attractions.
The three-bedroom, two-bathroom dwelling sleeps eight guests and boasts high-end furnishings, a chef's kitchen with top-of-the-line appliances, two large-screen TVs, and free off-street parking.