TOP 30 Berkshire vacations in Massachusetts

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

Welcome to Berkshire Rental Properties, located at 29 Benton Avenue in Great Barrington, Massachusetts. Whether you're in search of a quaint cottage or a luxurious multifamily estate, Berkshire Rental Properties offers a wide range of options to suit your needs. Our listings are carefully selected for their desirability, location, and top-notch amenities, providing a step above the typical rental offerings. At Berkshire Rental Properties, we understand the allure of the Berkshires and aim to provide a seamless getaway experience for our guests. Whether you're seeking outdoor adventures, cultural experiences, or simply a relaxing retreat, our properties serve as the perfect gateway to all that the Berkshires have to offer.

The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.

Berkshire Soccer Academy is a premier institution located at 620 Reservoir Road in Otis, Massachusetts, United States. As a real estate agency, we specialize in helping clients find the perfect properties for their needs. Our team of experienced agents is dedicated to providing exceptional service and guidance throughout the buying and selling process. Additionally, as a travel agency, we offer personalized travel packages and itineraries to ensure that our clients have unforgettable experiences. Whether you are looking for a new home or planning your next vacation, Berkshire Soccer Academy is here to help you every step of the way.

Berkshire Rivers Fly Fishing, located in Great Barrington, Massachusetts, is the go-to institution for fly fishing guides in Western Massachusetts and the Hudson Valley. With a focus on safety, fun, and, of course, fish, Berkshire Rivers offers private fishing trips that include all necessary gear, making it a hassle-free and enjoyable experience for all. Conveniently located within a comfortable drive from New York City and Boston, Berkshire Rivers provides fishing excursions in Berkshire County, New York's Hudson Valley, Southern Vermont, and Northwest Connecticut. Whether you're seeking a unique family adventure or hoping to reel in trophy northern pike or beautiful trout, Berkshire Rivers has something for everyone. Their excursions cater to beginners and experts alike, with customized trips to meet individual needs. With a reputation for top-notch teaching and exceptional customer service, Berkshire Rivers ensures that anglers leave not only with the satisfaction of a great catch but also with the knowledge and skills to continue enjoying the sport independently for years to come.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires is a charming lodging destination nestled in the picturesque town of Lee, Massachusetts. Surrounded by the stunning beauty of the Berkshires, this resort offers a perfect retreat for families and couples looking to relax and unwind in a peaceful setting. The resort features spacious accommodations, including comfortable rooms and suites, all equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a range of on-site facilities, including indoor and outdoor pools, a fitness center, tennis courts, and a game room. There are also organized activities and events for guests of all ages to enjoy.

Happy Place Berkshires is a charming clothing store located at 312 Main Street in Great Barrington, Massachusetts. Step into a world of colorful and stylish fashion where you can find the perfect outfit to express your unique personality. From trendy tops to cozy sweaters, our store offers a wide selection of clothing for men and women. Whether you're looking for a casual everyday look or a special outfit for a night out, Happy Place Berkshires has something for everyone. Come visit us and experience the joy of shopping in a welcoming and cozy environment.

Berkshire Hathaway HomeServices Barnbrook Realty is a prestigious real estate agency located in the charming town of Great Barrington, Massachusetts. Situated at 271 Main Street, this agency specializes in helping clients buy and sell residential properties in the picturesque Berkshire region. With a team of experienced and knowledgeable real estate professionals, Berkshire Hathaway HomeServices Barnbrook Realty provides top-notch service and guidance to clients looking to find their dream home or investment property. Whether you are a first-time homebuyer or a seasoned investor, this agency is dedicated to helping you navigate the real estate market with ease and confidence.

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.

Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is a welcoming lodging institution located in Lee, Massachusetts, United States. Situated at 165 Meadow Street, this resort offers a relaxing and comfortable environment for guests to enjoy during their vacation. The tour reception area provides guests with information about the resort's amenities and activities, ensuring a memorable stay for all visitors. With its convenient location and friendly staff, Holiday Inn Club Vacations Oak n’ Spruce Resort - Tour Reception is the perfect choice for those seeking a peaceful getaway in the beautiful Berkshires region.

Berkshire Valley Inn is a charming lodging located at 2541 Hancock Road in the picturesque town of Williamstown, Massachusetts. Surrounded by the stunning Berkshire Mountains, this cozy inn offers a peaceful retreat for guests looking to relax and unwind. The well-appointed rooms provide a comfortable and inviting atmosphere, perfect for a weekend getaway or a longer stay. Guests can enjoy the beautiful surroundings, explore nearby hiking trails, or visit the many attractions in the area. Whether you're seeking a quiet escape or an adventurous vacation, Berkshire Valley Inn is the perfect destination for your next trip to the Berkshires.

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.

Miraval Berkshires Resort & Spa is a luxurious wellness retreat nestled in the picturesque town of Lenox, Massachusetts. Situated at 55 Lee Road, this institution offers a serene escape for those seeking relaxation and rejuvenation. With a focus on health and well-being, guests can indulge in a variety of spa treatments, fitness classes, and healthy dining options. The resort also provides luxurious lodging accommodations, including spacious rooms and suites with modern amenities. Whether you're looking to unwind with a massage, practice yoga in a peaceful setting, or simply enjoy the tranquil surroundings, Miraval Berkshires Resort & Spa is the perfect destination for a restorative getaway.

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 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.

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.

Vacation Village in the Berkshires is a charming lodging institution located at 276 Brodie Mountain Road in Hancock, Massachusetts, United States. Nestled in the picturesque Berkshires region, this resort offers cozy accommodations and top-notch amenities for a relaxing and enjoyable vacation experience. Guests can unwind in spacious suites equipped with modern comforts, take a dip in the indoor or outdoor pools, or explore the nearby attractions such as ski slopes, hiking trails, and cultural venues. Whether you're seeking a romantic getaway or a fun family vacation, Vacation Village in the Berkshires is the perfect destination for your next trip.

Stay Berkshires is a charming lodging institution located at 1146 Cold Spring Road in the picturesque town of Williamstown, Massachusetts. Nestled in the heart of the Berkshires, our cozy accommodations offer a peaceful retreat for visitors looking to relax and unwind in a beautiful natural setting. Whether you're exploring the nearby cultural attractions or simply seeking a tranquil escape, Stay Berkshires provides a comfortable and inviting home away from home. Experience the warmth and hospitality of our friendly staff as you enjoy all that the Berkshires have to offer.

The Lake House Guest Cottages of the Berkshires is a charming retreat nestled on the shores of Pontoosuc Lake in Lanesborough, Massachusetts. This picturesque institution offers cozy and beautifully appointed cottages for overnight stays, providing guests with a peaceful and serene atmosphere to relax and unwind. The on-site restaurant serves delicious meals made with locally sourced ingredients, offering a taste of the region's culinary delights. Whether you're looking for a romantic getaway, a family vacation, or a solo escape, The Lake House Guest Cottages of the Berkshires is the perfect destination for a memorable and rejuvenating experience.

Berkshire Lakeside Lodge is a charming lodging located at 3949 Jacobs Ladder Road in Becket, Massachusetts. Situated in the stunning Berkshire Mountains, this cozy retreat offers guests a peaceful and serene escape surrounded by nature. With comfortable accommodations and beautiful views of the nearby lake, Berkshire Lakeside Lodge is the perfect destination for those looking to relax and unwind. Whether you're seeking a romantic getaway or a family vacation, this lodge provides a warm and welcoming atmosphere for all guests to enjoy.

Berkshire Pet Pals, LLC is a premier pet care service located at 45 Hartwood Road in Lee, Massachusetts, United States. Our team of experienced and dedicated professionals provide personalized care and attention to your furry friends, ensuring they are happy, healthy, and well-cared for while you are away. From dog walking to pet sitting, grooming, and more, we offer a range of services to meet the unique needs of your beloved pets. Trust Berkshire Pet Pals, LLC to provide top-notch care for your pets in a safe and loving environment.

Berkshire Homes and Condos is a reputable real estate agency located at 48 Saint Ann's Avenue in Lenox, Massachusetts, United States. Specializing in luxury homes and vacation condos in the picturesque Berkshire region, this agency offers exclusive listings and full property details for interested buyers and renters. With prices and inventory updated as of April 5, 2024, Berkshire Homes and Condos provides unparalleled service and expertise in the local real estate market. To access their full range of properties and continue your search, simply agree to their Terms of Use.

Jiminy Peak Vacation Home Rentals is a real estate and travel agency located at 37 Corey Road in Hancock, Massachusetts, United States. We offer cozy vacation homes perfect for winter weekends, holiday periods, and spring, summer, and fall getaways. For winter weekends and holiday periods, we require a 7-day cancellation notice with a 10% cancellation fee of the total reservation. For midweek stays during non-holiday periods, we require a 48-hour cancellation notice with the same cancellation fee policy.

Berkshire Hathaway HomeServices Island Properties Nantucket is a premier real estate agency located in the picturesque island of Nantucket, Massachusetts. Specializing in luxury properties and vacation rentals, our experienced team of agents are dedicated to helping clients find their dream home or perfect getaway on this charming island. With a commitment to exceptional service and a deep knowledge of the local market, Berkshire Hathaway HomeServices Island Properties Nantucket is the go-to agency for all your real estate needs on Nantucket. Visit us at 35A Old South Road to start your property search today.

Berkshire Hathaway HomeServices Robert Paul Properties Orleans is a real estate agency located at 414 South Orleans Road in Orleans, Massachusetts, United States. Situated in the heart of Cape Cod, Orleans is known for its picturesque harbors, beautiful beaches, and crystal-clear lakes. Our office is conveniently located where Route 39 meets Route 28 in South Orleans, making it easy for clients to access our services. Whether you are looking to sell your home or find your dream home on the Lower Cape, our experienced team is ready to assist you every step of the way. Visit us today and let us help you navigate the real estate market in this charming coastal town.

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.

Berkshire Whitewater is an exciting tourist attraction and travel agency located at 66 Thunder Mountain Road in Charlemont, Massachusetts, United States. Offering thrilling whitewater rafting adventures on the beautiful Deerfield River, Berkshire Whitewater is the perfect destination for outdoor enthusiasts looking for an adrenaline-pumping experience. With experienced guides and top-of-the-line equipment, visitors can enjoy a safe and unforgettable journey through the rapids. Whether you're a seasoned rafter or a first-timer, Berkshire Whitewater is the ultimate destination for an action-packed adventure in the heart of the Berkshires.

Berkshire Camino LLC is a premier institution located at 437 North Street in Pittsfield, Massachusetts, United States. We specialize in organizing and leading guided walking tours along the picturesque Berkshire Camino trail, offering a unique and enriching experience for outdoor enthusiasts and spiritual seekers alike. Our knowledgeable guides will lead you through stunning landscapes, historic sites, and charming towns, providing insight into the rich culture and natural beauty of the region. Join us for a transformative journey along the Berkshire Camino and discover the magic of this hidden gem in Western Massachusetts.