TOP 30 Family vacation packages 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.

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.

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.

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.

Fly Tringo is a premier travel agency located at 443 Crane Avenue in Pittsfield, Massachusetts. Our team of experienced travel experts are dedicated to providing exceptional service and personalized travel solutions to our clients. Whether you're planning a family vacation, romantic getaway, or business trip, Fly Tringo has you covered. From booking flights and accommodations to organizing tours and activities, we handle all the details so you can relax and enjoy your journey. Contact us today to start planning your next adventure!

Berkshire Travel Group is a premier travel agency located at 1450 East Street in Pittsfield, Massachusetts, United States. With a team of experienced travel experts, we provide personalized service and tailored travel packages to meet the unique needs of our clients. Whether you're looking to plan a relaxing beach getaway, an adventurous hiking trip, or a luxurious cruise vacation, we are here to help make your travel dreams a reality. Contact us today to start planning your next unforgettable journey with Berkshire Travel Group.

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.

Cruises Inc Eric Martin is a premier travel agency located in Pittsfield, Massachusetts. Specializing in luxury cruises, our experienced team led by Eric Martin will help you plan the perfect getaway on the high seas. With personalized service and attention to detail, we ensure that your cruise experience is unforgettable. Visit us at 42 Fourth Street to start planning your dream vacation today.

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!

Welcome to Berkshire Knapsackers, your ultimate destination for outdoor adventure and relaxation located at 11 Churchill Street, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and families alike. Explore our lush trails, perfect for hiking and bird watching, or enjoy a leisurely picnic amidst the stunning natural beauty. Whether you're seeking a peaceful retreat or an active day out, Berkshire Knapsackers provides a picturesque setting to reconnect with nature. Visit us today and discover the tranquility and charm of our beloved park.