Find short term rentals in Stockbridge, MA at the best prices

This family-friendly property is situated in Richmond, just 8km from the Tanglewood Music Center and 10km from Hancock Shaker Village, offering easy access to cultural attractions and outdoor activities.
This spacious five-bedroom apartment comfortably accommodates up to 10 guests, making it ideal for families or groups. The property offers a range of amenities including a fully equipped kitchen, a private garden, a hot tub, and a spa, ensuring a comfortable and enjoyable stay.

This studio apartment in Great Barrington is situated 300 meters from Main Street's shops and restaurants and a short trail from Lake Mansfield.
This 37 square meter studio can accommodate up to four guests, featuring a queen bed and futon, a private balcony with mountain views, an upright piano, and amenities including air conditioning and internet.

Eastover, a holistic retreat, offers a tranquil escape on 600 acres, situated just a few minutes from downtown Lenox.
This B&B provides complimentary wellness classes, a swimming pool, spa, fitness centre, and parking, with rooms featuring a double and a twin bed, alongside private bathrooms.

This South Lee flat offers a historic residential setting, located 5.9 kilometres from the Norman Rockwell Museum and 12.4 kilometres from Tanglewood Musical Centre.
With a floor area of 139 square metres, this two-bedroom apartment accommodates up to seven guests and includes a fully equipped kitchen, a washing machine, a fireplace, and complimentary private parking.

Eastgate Inn is a charming bed and breakfast located in Lenox, a short walk from the city centre and just a few kilometres from Tanglewood Music Centre, Frelinghuysen Morris House and Studio, and Lenox Library. The inn offers a peaceful and relaxing atmosphere, ideal for those seeking a tranquil escape from the hustle and bustle.
The Eastgate Inn features a comfortable and inviting common area with a library for quiet reading and a barbecue area for outdoor gatherings. Guests can enjoy free Wi-Fi and parking, as well as a flexible check-in process and personalised service from the friendly staff.

This Stockbridge holiday home enjoys a central location, within 1.6km of Schantz Galleries, the Housatonic River, and Mission House, and under 1.6km from the Berkshire Theatre Festival and Naumkeag Museum.
This five-bedroom, two-bathroom property sleeps twelve guests and boasts a fully equipped kitchen, free Wi-Fi, a fireplace, and a washing machine; housekeeping is available on request.

This South Lee flat provides easy access, situated a 5-minute walk from the Housatonic River and a 5-minute drive from Naumkeag Historic House.
This 139 square meter flat accommodates up to four guests with two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, on-site parking, and a fireplace for a comfortable stay.

This charming bed and breakfast is located in the mountains of Lenox, just a short drive from popular attractions like Shakespeare and Company, The Mount, and Kennedy Park. It has received excellent reviews from previous guests.
The accommodation offers a peaceful retreat with a beautiful garden and a cosy library. Guests can enjoy a continental breakfast, free Wi-Fi, and free parking, as well as barbecue facilities and a fireplace in the lobby.

Stockbridge Country Inn is located in the Berkshire countryside, just under a mile from the Norman Rockwell Museum and a half-mile from Chesterwood, making it a perfect base for exploring the area's cultural attractions. The inn consistently receives excellent ratings for its location, cleanliness, and overall experience.
The inn offers a single bedroom with a private bathroom and features a garden, terrace, swimming pool, and parking. Guests can enjoy a gourmet breakfast, relax in the peaceful countryside setting, and take advantage of the free Wi-Fi, concierge services, and nearby activities like golf and skiing.

This holiday home is located in the mountains of West Stockbridge, within a 5km radius of attractions such as Hoffman's Pottery and Chesterwood. It has received very good user ratings.
The house offers 3 bedrooms and 4 bathrooms, accommodating up to 6 guests, with a total floor area of 297 square metres. Guests can enjoy a fully equipped kitchen, a fireplace, a terrace, a garden, and free Wi-Fi.

This historic farmhouse, built in 1815 and listed on the National Register of Historic Places, is located in South Lee, 3 kilometres from downtown Lee and 3.2 kilometres from Stockbridge, offering mountain and river views from its shared yard and convenient access to Ski Butternut (16 kilometres), Bousquet Mountain (19 kilometres), October Mountain State Forest (9.7 kilometres), and the Appalachian Trail.
This 139 square metre residence provides 3 bedrooms and 2 bathrooms accommodating up to 5 guests, with features including a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, free WiFi, a washer/dryer, and keyless entry, while being family-friendly and pet-friendly for an additional fee.

The Chambery Inn is situated in Lee, Massachusetts, a short drive from both the Berkshire Scenic Railroad Museum and Tanglewood Musical Center, making it an ideal base for exploring the area's attractions. The inn has consistently received excellent ratings for its location, cleanliness, and overall experience.
This former schoolhouse has been transformed into a charming guesthouse with a unique design, featuring individual room styles and special features. Guests can enjoy a continental breakfast delivered to their room, relax in the garden, take advantage of the spa, and enjoy the nearby Ski Butternut resort for winter sports.