The Reel Retreat | Theatre & Firepit Game Room
apartment, Pittsfield
This four-bedroom, two-bathroom Pittsfield vacation rental is located in southern Pittsfield, minutes from downtown Pittsfield and Lenox, providing easy access to Tanglewood and Barrington Stage Company.
The 4-bedroom home boasts a private backyard, a fully equipped kitchen, a dedicated movie theater, a game room, and a deck with a grill, comfortably accommodating up to 7 guests and offering proximity to Bousquet Ski Area, Canoe Meadows, and Kennedy Park.
The 4-bedroom home boasts a private backyard, a fully equipped kitchen, a dedicated movie theater, a game room, and a deck with a grill, comfortably accommodating up to 7 guests and offering proximity to Bousquet Ski Area, Canoe Meadows, and Kennedy Park.
3 Acres, Mtn Views, Hot Tub, Steps To Winery
apartment, Richmond
This pet-friendly vacation home in Richmond is located a short walk from Balderdash Cellars and a 3-minute drive from Hancock Shaker Village, offering prime access for outdoor activities like kayaking and motor boating.
This 2740 sq ft apartment features 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests, with amenities including a full kitchen, air conditioning, a jacuzzi, a terrace, a garden, and on-site covered parking.
This 2740 sq ft apartment features 3 bedrooms, 2 bathrooms, and accommodates up to 6 guests, with amenities including a full kitchen, air conditioning, a jacuzzi, a terrace, a garden, and on-site covered parking.
Newly Renovated, And Spacious Great For Family
apartment, Pittsfield
This one-bedroom apartment is situated in downtown Pittsfield, just minutes from the Berkshire Museum and the vibrant restaurants and shops of North Street.
The apartment is newly renovated with modern furniture and appliances, including a private parking spot, a jacuzzi, and access control on all doors for added security.
The apartment is newly renovated with modern furniture and appliances, including a private parking spot, a jacuzzi, and access control on all doors for added security.
Cozy Pittsfield Gem W/ Deck, Gazebo & Fireplace!
apartment, Pittsfield
This 3-bedroom, 3-bathroom Pittsfield apartment offers convenient access to outdoor recreation, located 8 miles from Bousquet Mountain Ski Area and 12 miles from Jiminy Peak Mountain Resort, with Ashuwillticook Rail Trail just 1 mile away and Pittsfield State Forest 8 miles distant.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
Maries Place Unit 3
apartment, Pittsfield
This charming colonial house is located on a quiet street in southeast Pittsfield, just minutes from restaurants, shops, and major attractions like Hancock Shaker Village, MASS MoCA, and the Colonial Theatre. The home has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The three-bedroom house comfortably accommodates up to six guests, offering a spacious living room with a gas stove, a well-equipped kitchen, and a private backyard with a deck. Enjoy amenities like air conditioning, free Wi-Fi, and parking, making this a perfect base for exploring all that Pittsfield has to offer.
The three-bedroom house comfortably accommodates up to six guests, offering a spacious living room with a gas stove, a well-equipped kitchen, and a private backyard with a deck. Enjoy amenities like air conditioning, free Wi-Fi, and parking, making this a perfect base for exploring all that Pittsfield has to offer.
Spacious 4 Br+ House In The Heart Of Berkshires
apartment, Pittsfield
This five-bedroom, two-bathroom Pittsfield home offers easy access to hiking and skiing trails, and a short drive to Tanglewood.
The spacious residence, perfect for families or groups up to nine, boasts a fully equipped kitchen, ample parking, a well-maintained yard, and wheelchair accessibility via a ramp; nearby activities include exploring the Berkshires.
The spacious residence, perfect for families or groups up to nine, boasts a fully equipped kitchen, ample parking, a well-maintained yard, and wheelchair accessibility via a ramp; nearby activities include exploring the Berkshires.
Lakefront Home On Ponstoosuc Lake, The Berkshires
apartment, Lanesborough
This Lanesborough lake house boasts a prime Pontoosuc Lake location, offering 120 feet of private shoreline and proximity to Mount Greylock State Reservation (within 20 minutes).
The 2,600-square-foot home features three bedrooms, two bathrooms, sleeps eight, and includes a private dock, Weber grill, Roku TVs, and is near miniature golf, a driving range, and Krispy Kreme.
The 2,600-square-foot home features three bedrooms, two bathrooms, sleeps eight, and includes a private dock, Weber grill, Roku TVs, and is near miniature golf, a driving range, and Krispy Kreme.
Solomon Ely Homestead Set In Walkable Downtown
apartment, Pittsfield
This 1847 New England farmhouse rental in downtown Pittsfield offers convenient access to theaters, restaurants, and is a short drive from Tanglewood, Bousquet Ski Area, and Hancock Shaker Village.
The four-bedroom, one-bathroom house sleeps seven guests and features a kitchen with a fridge, freezer, and microwave, keyless entry, on-site host assistance, a spacious sunroom, wraparound porch, backyard deck, and a fire pit.
The four-bedroom, one-bathroom house sleeps seven guests and features a kitchen with a fridge, freezer, and microwave, keyless entry, on-site host assistance, a spacious sunroom, wraparound porch, backyard deck, and a fire pit.
Explore The Berkshires From This Charming Home.
apartment, Pittsfield
This centrally located accommodation in Pittsfield offers easy access to various attractions within short driving distances, including ski resorts, charming towns, and cultural attractions. Guests have rated this accommodation as excellent for its cleanliness and location.
The accommodation has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It features a fully equipped kitchen, air conditioning, parking, and access to streaming services. Guests can enjoy the charming towns nearby, visit cultural attractions, attend live music performances at Tanglewood, or go skiing at nearby resorts.
The accommodation has 2 bedrooms, 1 bathroom, and can accommodate up to 6 guests. It features a fully equipped kitchen, air conditioning, parking, and access to streaming services. Guests can enjoy the charming towns nearby, visit cultural attractions, attend live music performances at Tanglewood, or go skiing at nearby resorts.
The Oliver Wendell Holmes Guesthouse @ Holmesdale
apartment, Pittsfield
Historic Holmesdale Cottage is situated on 16 acres of a private estate on the Pittsfield/Lenox border, offering tranquility amidst the Berkshires. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom cottage accommodates up to four guests, featuring a king-size bed and a spiral staircase.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
Guests enjoy access to a pool, tennis court, and reflecting pond, along with modern conveniences like central AC/heat, high-end appliances, and a king-size iComfort mattress with luxury linens. The cottage retains original details like wood floors and a fireplace, while offering stunning views of the Berkshire mountains.
Marie's Place, Unit 1
apartment, Pittsfield
This Pittsfield apartment is conveniently located just a 7-minute drive from the Bosquet ski area and 28 minutes from Jiminy Peak, making it ideal for winter sports enthusiasts. The apartment enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 3-bedroom rental can accommodate up to 6 guests and features a spacious eat-in kitchen and living room. Enjoy the enclosed front porch or the small outside deck, relax with the provided wet towel basket, and take advantage of the off-street parking for two cars.
This 3-bedroom rental can accommodate up to 6 guests and features a spacious eat-in kitchen and living room. Enjoy the enclosed front porch or the small outside deck, relax with the provided wet towel basket, and take advantage of the off-street parking for two cars.
Historic Stone Church In The Berkshires
apartment, Lanesborough
Hinterland Hall, a unique conversion of an 1836 church, is located in Lanesborough, Massachusetts, minutes from Jiminy Peak Mountain Resort and a short drive from Mass MoCA and The Clark art museums.
This luxurious Lanesborough castle offers one bedroom, two bathrooms, and accommodates two guests, featuring a fully equipped kitchenette, a stone patio with a fire pit, and a luxurious ensuite bathroom with a soaking tub and rain shower; nearby activities include skiing at Jiminy Peak and exploring renowned cultural attractions.
This luxurious Lanesborough castle offers one bedroom, two bathrooms, and accommodates two guests, featuring a fully equipped kitchenette, a stone patio with a fire pit, and a luxurious ensuite bathroom with a soaking tub and rain shower; nearby activities include skiing at Jiminy Peak and exploring renowned cultural attractions.
