TOP 30 Family friendly vacation in Pittsfield, Massachusetts

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, is a charming lodging option located at One West Street in Pittsfield, Massachusetts, United States. This hotel offers comfortable accommodations and a range of amenities for both business and leisure travelers. Guests can enjoy spacious rooms and suites, a fitness center, on-site dining options, and convenient access to local attractions such as Tanglewood, Norman Rockwell Museum, and the Berkshire Museum. With its prime location and excellent service, Holiday Inn & Suites Pittsfield-Berkshires is the perfect choice for a relaxing stay in the heart of the Berkshires.

The Hilton Garden Inn Lenox Pittsfield is a comfortable and modern lodging establishment located at 1032 South Street in Pittsfield, Massachusetts. This hotel offers a convenient location for guests looking to explore the beautiful Berkshires region. The hotel features spacious and well-appointed rooms, a fitness center, an indoor pool, and a delicious on-site restaurant. Whether you are traveling for business or leisure, the Hilton Garden Inn Lenox Pittsfield provides a relaxing and enjoyable stay for all guests.

The Pittsfield Visitor Center is a local government office and travel agency located at 28 Renne Avenue in Pittsfield, Massachusetts. This institution serves as a hub for tourists and locals alike, providing information on attractions, events, and accommodations in the area. Whether you're looking for recommendations on where to eat, what to see, or where to stay, the knowledgeable staff at the Pittsfield Visitor Center is ready to assist you in making the most of your visit to this charming New England town. Stop by for maps, brochures, and personalized recommendations to help you explore all that Pittsfield has to offer.

Welcome to Pittsfield State Forest, a breathtaking natural haven located at 123-221 Potter Mountain Road, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and adventure seekers alike. Spanning over 11,000 acres, Pittsfield State Forest is home to lush woodlands, sparkling streams, and stunning vistas that promise to captivate visitors of all ages. Explore a myriad of recreational activities, including hiking, mountain biking, and horseback riding along our extensive trail network. During the warmer months, enjoy picnicking, camping, and fishing in the tranquil setting of Berry Pond, the highest natural body of water in the state. In the winter, embrace the snowy landscape with opportunities for cross-country skiing and snowmobiling.

Located in the picturesque town of Pittsfield, Massachusetts, the Best Western Plus Berkshire Hills Inn & Suites offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. Situated at 1350 West Housatonic Street, this hotel provides guests with a convenient location near popular attractions such as Tanglewood, Hancock Shaker Village, and the Norman Rockwell Museum. The hotel features spacious rooms and suites equipped with amenities such as free Wi-Fi, flat-screen TVs, and mini fridges. Guests can also enjoy a complimentary hot breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Best Western Plus Berkshire Hills Inn & Suites provides a welcoming and relaxing atmosphere for all guests.

Courtyard by Marriott Lenox Berkshires is a charming lodging option located at 70 Pittsfield Road in Lenox, Massachusetts, United States. Situated in the beautiful Berkshires region, this hotel offers modern amenities and comfortable accommodations for guests looking to explore the area's cultural attractions, outdoor activities, and scenic landscapes. With spacious rooms, a fitness center, indoor pool, and on-site dining options, Courtyard by Marriott Lenox Berkshires is the perfect choice for travelers seeking a relaxing and convenient stay in this picturesque New England town.

The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.

Berkshire Mountain Lodge is a charming lodging institution located at 8 Dan Fox Drive in Pittsfield, Massachusetts. Situated in the beautiful Berkshires region, the lodge offers a perfect blend of cultural attractions, historical sites, and natural beauty. Guests can explore nearby attractions such as The Mount, the former estate of American author Edith Wharton, and Tanglewood, the summer home of the Boston Symphony Orchestra. Berkshire Mountain Lodge is a family-friendly vacation destination that offers a variety of amenities and activities for guests of all ages. The resort has received numerous awards, including the RCI Gold Crown Status, Tripadvisor's Travelers' Choice Award, and the Hotels.com Loved by Guests Award, all of which recognize the exceptional service and hospitality provided by the lodge.

Howard Johnson by Wyndham Lenox is a charming lodging facility located at 462 Pittsfield Road in Lenox, Massachusetts. Situated in the beautiful Berkshires region, this hotel offers comfortable and affordable accommodations for travelers looking to explore the area. Guests can enjoy spacious rooms, complimentary breakfast, free Wi-Fi, and a seasonal outdoor pool. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Howard Johnson by Wyndham Lenox is the perfect choice for a relaxing getaway in Massachusetts.

Life House, Berkshires is a charming lodging located at 194 Pittsfield Road in Lenox, Massachusetts. Nestled in the picturesque Berkshires region, this institution offers a peaceful and serene retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a welcoming atmosphere for visitors to relax and unwind. With its convenient location and warm hospitality, Life House, Berkshires is the perfect destination for a memorable getaway in the heart of the Berkshires.

Knights Inn Lenox is a charming lodging establishment located at 474 Pittsfield Road in Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and excellent service to ensure a pleasant stay for guests. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's attractions, including Tanglewood, Norman Rockwell Museum, and the beautiful landscapes of the region. With its affordable rates and welcoming atmosphere, Knights Inn Lenox is the perfect choice for travelers looking for a relaxing retreat in western Massachusetts.

Berkshire Yankee Suites is a charming lodging establishment located at 20 West Housatonic Street in the picturesque city of Pittsfield, Massachusetts. Our suites offer a cozy and comfortable stay for travelers looking to explore the beautiful Berkshire region. Each suite is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. Our convenient location allows guests easy access to local attractions, dining options, and outdoor activities. Whether you are visiting for business or pleasure, Berkshire Yankee Suites is the perfect home away from home in the heart of the Berkshires.

Bonnie Brae Campground is a picturesque retreat nestled in the heart of Pittsfield, Massachusetts. Located at 108 Broadway Street, this charming campground offers a peaceful escape for nature lovers and outdoor enthusiasts. With spacious campsites, cozy lodging options, and beautiful park amenities, Bonnie Brae Campground is the perfect destination for a weekend getaway or extended vacation. Whether you prefer hiking through the lush forests, fishing in the nearby lakes, or simply relaxing by the campfire, this campground has something for everyone. Come experience the beauty and tranquility of Bonnie Brae Campground in Pittsfield, Massachusetts.

Anywhere Anyway Travel is a premier travel agency located on First Street in Pittsfield, Massachusetts. Our experienced team of travel experts is dedicated to helping you plan the perfect getaway, no matter where you want to go or how you want to get there. From booking flights and accommodations to organizing tours and excursions, we can handle all the details so you can relax and enjoy your trip. Let Anywhere Anyway Travel turn your travel dreams into reality.

Located in Pittsfield, Massachusetts, Berkshire Hills Country Club is a friendly and family-oriented private club offering an 18-hole golf course, a large swimming pool, and dining in the member's tavern. The clubhouse boasts spectacular panoramic views, making it a perfect venue for weddings and special events. The golf course and event space have been recognized as the "Best of the Berkshires" in the Berkshire Eagle Readers Poll. Founded in 1925, Berkshire Hills Country Club is the only A.W. Tillinghast designed golf course in Massachusetts. With over 30 weddings hosted in the past year, Berkshire Hills is a premier wedding venue in Berkshire County. The club offers three types of membership: Golf, Swim, and Social, as well as corporate memberships for businesses. Whether you're looking to play a round of golf, relax by the pool, or host a special event, Berkshire Hills Country Club has something for everyone. Operating hours are Monday to Saturday from 11:00am to 8:00pm and Sunday from 11:00am to 6:00pm.

Onota Boat Livery is a store located at 463 Pecks Road in Pittsfield, Massachusetts, United States. This institution offers a wide range of boat rental services, including canoes, kayaks, paddleboards, and motorboats, to help you explore the beautiful Onota Lake. Whether you're looking for a relaxing day on the water or an adventurous fishing trip, Onota Boat Livery has everything you need to make your experience unforgettable. Their friendly and knowledgeable staff are always ready to assist you with any questions or concerns you may have. Visit Onota Boat Livery today and start your next aquatic adventure!

Richmond Town Beach is a beautiful park located on Town Beach Road in Pittsfield, Massachusetts, United States. This picturesque beach offers stunning views of the surrounding landscape and a serene atmosphere perfect for relaxation and recreation. Visitors can enjoy swimming in the crystal-clear waters, sunbathing on the sandy shores, or picnicking in the shaded areas. With its well-maintained facilities and peaceful setting, Richmond Town Beach is the ideal destination for a day of fun in the sun with family and friends.

Bousquet Mountain Ski Area is a popular winter sports destination located at 101 Dan Fox Drive in Pittsfield, Massachusetts, United States. This family-friendly ski resort offers a variety of slopes for all skill levels, from beginner to expert, as well as a terrain park for snowboarders and freestyle skiers. With stunning views of the surrounding Berkshire Mountains, Bousquet Mountain Ski Area provides a fun and exciting atmosphere for visitors to enjoy skiing, snowboarding, and other winter activities. The resort also offers ski lessons, equipment rentals, and a cozy lodge with a fireplace to warm up after a day on the slopes. Whether you're a seasoned skier or trying it for the first time, Bousquet Mountain Ski Area is the perfect place to experience the thrill of winter sports.

Welcome to Camp Arrow Wood, your premier destination for outdoor adventure and relaxation in the heart of the Berkshires! Nestled at 195 Cloverdale Street, Pittsfield, Massachusetts, our camp offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a weekend getaway, a summer retreat, or a place to connect with nature, Camp Arrow Wood is the perfect spot. Our beautiful grounds boast a variety of amenities and activities for all ages. Explore our extensive hiking trails, enjoy a leisurely paddle on our scenic lake, or challenge yourself with our ropes course and climbing wall. For those looking to unwind, our tranquil setting provides the ideal backdrop for meditation, yoga, or simply soaking in the natural beauty.

Welcome to Allendale Pines MHC, your premier destination for comfortable and convenient lodging in the heart of the Berkshires. Nestled at 245 Cheshire Road in Pittsfield, Massachusetts, our RV park offers a serene and picturesque setting, perfect for both short visits and extended stays. Whether you're traveling in an RV or seeking a peaceful getaway, Allendale Pines provides a welcoming environment with modern amenities to meet all your needs. Our park features spacious sites equipped with full hookups, ensuring a hassle-free experience for all our guests. Enjoy the tranquility of our beautifully landscaped grounds, complete with walking paths and picnic areas that allow you to immerse yourself in nature. Conveniently located near local attractions, dining, and shopping, Allendale Pines MHC serves as an ideal base for exploring the vibrant culture and scenic beauty of the Berkshires.

Welcome to Berkshire U-Drive Boat Rental Discover the ultimate boating experience on Pontoosuc Lake with Berkshire U-Drive Boat Rental. Nestled in the picturesque hills of the Appalachian Mountains, our location offers breathtaking views and pristine waters, perfect for any adventure. Whether you're seeking a thrilling day on the lake or a serene sunset cruise, we have the ideal boat to suit your needs.

Welcome to Suzanne Crerar at Stone House Properties, your premier real estate partner located at 38 Main Street, West Stockbridge, Massachusetts. Serving the beautiful regions of Berkshire County, Massachusetts, and Columbia County, New York's Upper Hudson Valley, we are a well-established brokerage firm dedicated to providing exceptional services for both buyers and sellers. Our region is renowned for its breathtaking natural beauty, with the Berkshires and Upper Hudson Valley offering picturesque landscapes of rolling hills and expansive valleys. In addition to the stunning scenery, our area is rich in cultural landmarks, including Tanglewood, MASS MoCA, and the Olana State Historic Site, making it a truly desirable location for your next home.

Welcome to Barb Hassan Realty, Inc. Nestled in the heart of the beautiful Berkshires, Barb Hassan Realty, Inc. is your premier full-service real estate agency located at 31 Wendell Avenue, Pittsfield, Massachusetts. With over 35 years of dedicated service to the Northern, Central, and Southern Berkshire areas, we pride ourselves on offering professional, courteous, and responsive real estate services.

Welcome to Barb Hassan Realty, Inc. – Your Trusted Real Estate Partner in the Berkshires Located at 69 South Main Street, Lanesborough, Massachusetts, Barb Hassan Realty, Inc. is your local, full-service real estate agency dedicated to serving the vibrant community of the Berkshires. With over 35 years of experience in the real estate industry and more than $155 million in career sales, our team is committed to providing professional, courteous, and responsive services for all your real estate needs.