Holiday Rentals in Stockbridge, MA

About: 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.

About: This four-bedroom house is situated in a peaceful neighbourhood in Lee, within easy walking distance of the town centre and Lee Beach, making it ideal for exploring the area. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.

This spacious home comfortably accommodates up to nine guests, offering a generous layout with four bedrooms, two and a half bathrooms, a well-equipped kitchen, and a dedicated gym. Enjoy a range of amenities including high-speed Wi-Fi, streaming services, a movie theatre, and a sunny garden with fruit trees, perfect for relaxing after a day of exploring.

About: The Holiday Inn Club Vacations Oak N Spruce Resort in the Berkshires is situated in a peaceful setting about 25 miles from Adams, offering a tranquil escape from the city. This 3-star hotel has received very good user ratings for its cleanliness and overall experience.

The resort offers a range of accommodation options, including rooms with kitchens for added convenience. Guests can enjoy various amenities, such as a swimming pool, jacuzzi, tennis court, and fitness centre, as well as a restaurant and bar for dining and relaxation.

About: This studio apartment is located in the Berkshires, a short drive from cultural attractions like Kripalu, Tanglewood, and Lenox town. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.

The self-catering apartment is ideal for a small family or group of friends, accommodating up to three guests. It comes with a range of amenities including a private patio with a fire pit, a fully equipped kitchen, and a garden, as well as access to a fitness centre and parking.

About: Holiday rental listing for 4 guests with an excellent rating of 95% based on 27 reviews. This accommodation is based in Lee.

Facilities and services: a fitness center, an iron and free parking.

About: This apartment is in the centre of Lenox, just a short walk from Tanglewood, Shakespeare & Co, Kennedy Park, restaurants and shops, and 7 minutes from Bousquet Mountain. The apartment has excellent user, location and cleanliness ratings.

The apartment has 3 bedrooms and 1 bathroom, making it ideal for families or groups of up to 5 guests. It has a private entrance, a garden, parking, a fully equipped kitchen, air conditioning, internet, and a deck with a view over Lenox.

About: This charming cottage is situated in the heart of the Berkshires, just three miles from Tanglewood and within easy reach of other attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.

This cosy retreat features a bedroom and bathroom, perfect for couples seeking a peaceful getaway. The cottage offers a private deck and screened-in porch for enjoying the fresh air, along with WiFi and cable TV for entertainment.

About: This charming three-bedroom apartment is situated on a quiet dead-end street in central Lenox, a short walk from the town centre, Tanglewood, and Canyon Ranch. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.

The apartment is spacious and comfortably accommodates up to six guests. It features a well-equipped kitchen, a cosy living area with a fireplace, and a private garden with a deck, perfect for relaxing or entertaining.

About: This five-bedroom, six-bathroom holiday home is situated in Lee, a rural Berkshire town, just a short drive from Stockbridge and Lenox. It has received excellent ratings for its location, cleanliness and overall user experience.

The spacious property, covering 325 square metres, offers a range of amenities including a fully equipped kitchen, a terrace, a garden, a sauna, parking and a BBQ area. Guests can enjoy a range of activities in the surrounding area, including skiing, golfing, mountain biking, and exploring cultural attractions.

About: This charming barn is situated in Stockbridge, a short drive from Lee Premium Outlets, Lenox, and Kripalu, offering easy access to both shopping and cultural attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.

The self-catering accommodation is ideal for couples, with a private entrance, porch, and a cosy indoor yoga nook. Guests can enjoy a range of amenities, including a kitchen with a fridge, microwave, and stovetop, as well as a washer and dryer, plus high-speed Wi-Fi and electric heating.

About: 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.

About: This renovated loft on October Mountain is a short drive from Lenox, Lee and Great Barrington, offering a peaceful retreat in the heart of the Berkshires. The property has received excellent ratings for its location, cleanliness and overall experience.

The 800 square foot loft comfortably accommodates up to three guests and features a modern kitchen, a spacious living area and a private bathroom with a clawfoot tub. Enjoy the stunning views, unwind by the fire pit, explore the surrounding trails and discover the nearby cultural attractions.

About: This timeshare apartment in Lee, Massachusetts is conveniently located within a short drive of Albany, Boston, and New York City, making it a great base for exploring the region. It has received excellent ratings for its cleanliness, location, and overall experience.

The property offers a comfortable and spacious living space with three bedrooms, two bathrooms, and a living room with a sofa bed, comfortably accommodating up to six guests. Guests can enjoy a range of amenities, including swimming pools, a Jacuzzi, a fitness centre, a garden, and parking.

About: This charming one-bedroom apartment is situated just four miles from the town of Great Barrington, offering a peaceful retreat in a quiet lane. The property has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.

The apartment has a private bathroom, a small kitchen with a fridge, microwave, coffee maker and kettle, and a comfortable living area. Guests can enjoy a private patio with a fire pit, relax in the recreation room with a piano and pool table, or take advantage of the swimming pool during the summer months.

About: This spacious five-bedroom holiday home is conveniently located in Lee, close to the city centre and a lake, offering easy access to local attractions, shops and restaurants. The property has received excellent ratings for its cleanliness, location and overall user experience.

The apartment is perfect for large families or groups, with multiple living areas, a fully equipped kitchen and a Florida room leading to a deck overlooking the pool. Guests can enjoy a range of on-site amenities, including a swimming pool, fitness centre and garden, as well as explore the nearby ski resorts, cultural sites and attractions.

About: This charming apartment is situated in Lenox, a short distance from popular ski areas like Bousquet and Butternut, making it ideal for a winter getaway. The apartment is located in a beautifully renovated 1840 Victorian home, offering a unique and charming experience. This cosy flat has a private entrance and a fenced-in patio, perfect for relaxing outdoors. The apartment is equipped with a full kitchen, a shared swimming pool, a large backyard with a fire pit, a shared garden, and laundry facilities.

About: The Holiday Inn Club Vacations Oak N Spruce Resort In The Berkshires An Ihg Hotel is located in Lee, Massachusetts, just four kilometres from the town centre, offering a peaceful escape from the bustle of city life. The resort is surrounded by beautiful natural scenery, making it a perfect base for exploring the Berkshires.

The resort offers a range of self-catering accommodation options for up to two guests. The resort has a variety of amenities, including an indoor and outdoor pool, a fitness centre, a sauna, a picnic area and barbecue grills, as well as a business centre and a playroom for children.

About: This apartment is located just a short distance from Great Barrington, offering a peaceful retreat surrounded by fields, woods and a lake. The area is ideal for those seeking a tranquil escape from the hustle and bustle.

The spacious apartment can comfortably accommodate up to nine guests and features five bedrooms and two bathrooms. Enjoy a range of amenities including a kitchen, swimming pool, parking and internet access, as well as the chance to explore the surrounding natural beauty.

About: This spacious four-bedroom home in Lee is ideally located close to local amenities, making it a great choice for families or groups. It has consistently received excellent reviews for its cleanliness, location, and overall experience.

The apartment comfortably accommodates up to nine guests and offers a range of amenities to ensure a pleasant stay. Guests can enjoy a private pool, a large yard, a play area for children, and a well-equipped kitchen with a dishwasher, fridge, and microwave.

About: This charming house is located just a short drive from the Cranwell Spa & Golf Club, Norman Rockwell Museum, and Tanglewood, offering easy access to the area's cultural attractions. The peaceful surroundings provide a tranquil escape from the hustle and bustle of city life.

This four-bedroom, three-bathroom property comfortably accommodates up to nine guests, with a spacious 232 square metres of living space. Guests can enjoy a private pool, a fully equipped kitchen, and complimentary Wi-Fi access.

About: This fully renovated house is located on a quiet street in Lee, Massachusetts, just a short drive from both Lee Center and Lenox Center, offering a peaceful retreat in a convenient location. It has received excellent ratings for user experience, location, and cleanliness.

The spacious property spans 260 square metres and comfortably accommodates up to 11 guests across five bedrooms and three bathrooms. Guests can enjoy a well-equipped kitchen, a family room with a pool table, a terrace, a garden, parking, and air conditioning, making it perfect for families and groups seeking a comfortable and enjoyable stay.

About: This five-bedroom home is situated in Lenox, just a short walk from the town centre and two miles from Tanglewood, offering a peaceful retreat in a vibrant location. The property has consistently received excellent ratings for user experience, location, and cleanliness.

The spacious apartment, spanning 242 square metres, comfortably accommodates nine guests. Amenities include a fully equipped kitchen, a jacuzzi, a garden, a spa, parking, and internet access, ensuring a relaxing and enjoyable stay.

About: This apartment in Stockbridge is ideally located just a short walk from the Norman Rockwell Museum and Chesterwood, offering easy access to these popular attractions. The property boasts excellent ratings for location, cleanliness, and overall user experience.

This spacious three-bedroom flat comfortably accommodates up to six guests, with flexible sleeping arrangements including a den that can be used as a twin bedroom. The apartment features a well-equipped kitchen, air conditioning, parking, and internet access, ensuring a comfortable and enjoyable stay.

About: Apartment rental listing for up to 6 people with an excellent rating of 99% based on 114 reviews. This accommodation is located in Lenox.

Facilities and services: a kitchen, a washing machine and a coffee place. This is a family-friendly apartment!

About: This charming house in Stockbridge is just a short drive from Lee Premium Outlets, Lenox Center, and Canyon Ranch, placing you near a range of attractions and shopping opportunities. The house has consistently received excellent ratings for its cleanliness, location, and overall guest experience.

The property offers a private entrance and separate living space for up to four guests. It features a fully equipped kitchen, modern appliances, a private porch, and a garden, making it a comfortable and convenient option for your stay.

About: This charming cottage is situated in a private lake community near Stockbridge, a short walk from the Stockbridge Bowl and within easy reach of Tanglewood, Lenox, and downtown Stockbridge. The property has received excellent ratings for its location, cleanliness, and overall experience, making it an ideal choice for a relaxing getaway.

The cottage offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy modern amenities, a peaceful forest setting, lakefront access, hiking trails, and outdoor amenities such as a back deck, fire pit, screened-in porch, BBQ, and a kayak for exploring the lake.

About: This family-friendly house is located in Stockbridge, a short walk from the Housatonic River and Schantz Galleries, offering easy access to both nature and art. It has received excellent user ratings, making it a popular choice for travellers.

The property has three bedrooms and three bathrooms, spanning 172 square metres and comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a terrace, a garden, and a jacuzzi, offering a range of options for relaxation and entertainment.

About: This charming house is located in Lee, just a short walk from the Berkshire Mountain Country Store and Animagic Museum of Animation, with the Lee Library and Housatonic River within easy reach. The property has received excellent guest reviews, highlighting its comfortable and convenient features.

The two-bedroom property can comfortably accommodate up to four guests, making it ideal for families or friends travelling together. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private patio, a shared garden, and barbecue facilities, perfect for relaxing and enjoying the beautiful surroundings.

About: This ground-floor flat is conveniently located in Stockbridge, just minutes from Kripalu Center for Yoga & Health, Tanglewood, and the Stockbridge Bowl. The property has received excellent ratings for location, cleanliness, and overall user experience.

The two-bedroom property can accommodate up to six guests and features a fully equipped kitchen, a gas fireplace, a large yard, and pet-friendly policies. Guests can enjoy outdoor space, cook meals in the well-equipped kitchen, and relax by the fireplace.

About: Holiday rental listing for up to 8 guests with an excellent rating of 97% based on 29 reviews. You will be based in Great Barrington.

Services and facilities: an iron, a jacuzzi and free parking. This apartment in Great Barrington also has air conditioning!

About: This four-bedroom lakeside home is located just a short distance from Lenox, offering easy access to the town's attractions and the scenic beauty of the Berkshires. The property has received consistently high ratings for its location, cleanliness, and overall experience, making it an ideal choice for families or groups seeking a comfortable and enjoyable stay.

The spacious property features a large living area, a separate lounge with a fireplace, and a dining area that can comfortably accommodate up to ten guests. Amenities include two kayaks, four life jackets, a full-size laundry, central air conditioning, parking for four vehicles, and a fully equipped kitchen with stainless steel appliances, a gas stove, and an abundance of cookware and utensils.

About: This charming lakeside home in Lenox is situated a short distance from The Mount and Ventfort Hall Mansion, offering easy access to the area's historic attractions and cultural offerings. It has received excellent ratings from previous guests, making it a popular choice for travellers seeking a comfortable and convenient stay.

The four-bedroom property spans 176 square metres and comfortably accommodates up to ten guests. A spacious living area with a fireplace, a fully equipped kitchen, a private garden, and a deck with a BBQ grill provide ample space for relaxation and entertaining.

About: This apartment is conveniently located in Stockbridge, just a short distance from Tanglewood, Stockbridge Town Beach, and the town centre. With excellent user, location, and cleanliness ratings, you can expect a comfortable and enjoyable stay.

This three-bedroom property can comfortably accommodate up to six guests. It comes equipped with a modern kitchen, a spacious sun deck, a fire pit, a BBQ grill, a main floor bedroom, a bonus office/playroom, and a game table, ensuring a memorable stay for all.

About: This charming apartment is located in Stockbridge, within easy reach of the town's main attractions, including the Stockbridge Bowl, the Norman Rockwell Museum, and the Berkshire Botanical Garden. The apartment has received excellent ratings for its location, cleanliness, and overall experience.

The apartment offers four bedrooms and two bathrooms, accommodating up to eight guests. It features a well-equipped kitchen, multiple living spaces, and expansive outdoor decks, making it perfect for families or groups of friends looking for a comfortable and enjoyable stay in the Berkshires.