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

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.

This boutique inn is located in central Lenox, Massachusetts, offering direct walking access to shops and restaurants, and is only 3 kilometres from Tanglewood.
This pet and family-friendly establishment offers 1 bedroom and 1 bathroom for up to 2 guests, featuring air conditioning, Wi-Fi, a garden, and parking, with communal areas including a wraparound porch, a living room with games, and an outdoor fire pit, plus a dedicated children's playroom.

This secluded apartment, located on a quiet dead-end road in Stockbridge, offers a peaceful retreat with easy access to woodland and a stream, ideal for those seeking a tranquil getaway.
This pet-friendly flat accommodates up to six guests and features a well-equipped kitchen, air conditioning, two bathrooms, and an outdoor deck, with ample garden space for recreation and exploration.

The Whistler's Inn is a charming bed and breakfast situated in Lenox, Massachusetts, a short distance from Tanglewood Musical Center and Shakespeare & Company Theater. The inn has consistently received very good user ratings for its cleanliness and excellent location.
Each room at the inn has a unique style and features a private bathroom. Guests can enjoy a daily gourmet breakfast, afternoon tea and cookies, and have access to a parlour room with a piano and a library. The inn also has a garden and a terrace, and guests can enjoy free Wi-Fi and parking.

This rural Housatonic holiday home in West Stockbridge is situated 644 metres from the Housatonic River and 1.29 kilometres from the Norman Rockwell Museum.
This 296 square metre detached house, accommodating up to 9 guests, features 4 bedrooms, 4 bathrooms, a heated swimming pool, hot tub, garden, terrace, barbecue, free Wi-Fi, air conditioning, and a fully equipped kitchen.

This four-bedroom, three-bathroom flat in Lenox, situated in the Berkshires, offers picturesque views of a wildflower meadow and mountains, located a short drive from downtown Lenox and Tanglewood.
Accommodating up to 12 guests, this residence features a well-equipped kitchen, a 28-square-meter screened porch, and a peaceful garden, with amenities including internet, air conditioning, and parking.

This B&B, The Red Lion Inn, is located in Stockbridge's town centre, offering easy access to shops and cultural sites, and is situated 3.2 kilometres from the Norman Rockwell Museum and 1.6 kilometres from the Berkshire Botanical Garden.
This accommodation provides a swimming pool, jacuzzi, fitness centre, and on-site dining, with individually decorated suites accommodating up to four guests, and offers complimentary bicycle hire for exploring the area.

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 house, situated in the historic district of Stockbridge, Massachusetts, is a short walk from the Divine Mercy Shrine and a short drive from other popular attractions like the Norman Rockwell Museum. The surrounding area offers a peaceful and picturesque setting, perfect for a relaxing getaway.
This five-bedroom, two-bathroom property can accommodate up to 13 guests, providing ample space for families or groups of friends. The house offers a fully equipped kitchen, laundry facilities, and a peaceful garden, ensuring a comfortable and convenient stay.

This charming bed and breakfast is ideally situated in Lenox, just a short walk from Tanglewood, Kripalu Center for Yoga & Health, and the town centre. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The guest house has one bedroom and one bathroom, comfortably accommodating up to two guests. Amenities include air conditioning, internet access, a garden, and parking, ensuring a comfortable and enjoyable stay.

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 apartment-style lodging is located in the scenic Berkshires, offering a New England atmosphere near Lee.
The accommodation features two bedrooms and two bathrooms, accommodating up to six guests with a fully equipped kitchen, indoor and outdoor pools, a hot tub, a cinema, and the Beartree Bar, with free parking and a $10 per night resort fee plus tax for amenity access.

This renovated Lenox village half-duplex, near Wyndhurst Golf & Club (under 2km) and Lenox town centre (under 3km), offers easy access to Tanglewood (within 6km).
The three-bedroom property sleeps six, boasting a spacious layout with granite kitchen, two smart TVs, two guaranteed parking spaces, private porches, and a custom-tiled bathroom; nearby attractions include Canyon Ranch and the Lee Outlets.

This Stockbridge guesthouse offers a convenient base, situated 5.9 kilometres from Cranwell Spa & Golf Club, 6.9 kilometres from the Norman Rockwell Museum, and 9 kilometres from Tanglewood Musical Center.
Guests can enjoy family rooms with air conditioning and balconies, a fitness centre, an outdoor swimming pool, and a diverse breakfast menu, with complimentary WiFi available in public areas.

This Bed and Breakfast in downtown Lenox, Massachusetts, offers immediate walkability to local restaurants and boutiques, and is a convenient 3-minute drive to Tanglewood.
This establishment provides a private one-bedroom, one-bathroom suite for two guests, with amenities including air conditioning, Wi-Fi, a garden, and parking, alongside communal spaces such as a wraparound porch and a fire pit.

This 3-bedroom house is located in Lenox, just 0.8 kilometres from restaurants, shops, galleries, and hiking trails and 2.4 kilometres from Tanglewood and other cultural attractions. The property enjoys excellent ratings for location, cleanliness, and user experience.
The house offers ample space for families or groups of friends with its 3 bedrooms and 2 bathrooms, comfortably accommodating up to 5 guests. The property includes internet, a kitchen, air conditioning, parking, and is close to a range of activities and attractions.