TOP 30 Berkshires getaway in Massachusetts

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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.

Hume Christian Camp & Retreat Center in the Berkshires is a peaceful and serene institution nestled in the heart of Monterey, Massachusetts. This campground and retreat center offers a variety of activities and amenities for visitors to enjoy, including health and wellness programs, comfortable lodging options, and beautiful park-like surroundings. Whether you're looking to relax and unwind or participate in outdoor adventures, Hume Christian Camp & Retreat Center is the perfect destination. Come and experience the beauty and tranquility of this popular tourist attraction located at 73 Chestnut Hill Road in the Berkshires.

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.

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.

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.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

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.

The Heart of the Berkshires Motel is a charming lodging option located at 970 West Housatonic Street in Pittsfield, Massachusetts. Situated in the heart of the picturesque Berkshires region, this motel offers cozy and comfortable accommodations for travelers looking to explore the natural beauty and cultural attractions of the area. With a convenient location and friendly staff, the Heart of the Berkshires Motel is the perfect place to relax and unwind during your visit to the United States.

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.

Berkshire Inns is a charming lodging institution located at 461 Pittsfield Road in Lenox, Massachusetts, United States. Offering comfortable and cozy accommodations, Berkshire Inns provides a peaceful retreat for guests looking to explore the beautiful Berkshires region. With its convenient location and welcoming atmosphere, Berkshire Inns is the perfect choice for travelers seeking a relaxing stay in the heart of New England.

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 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 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.

Berkshires Week is a premier travel agency located at 75 South Church Street in Pittsfield, Massachusetts. Specializing in curated travel experiences in the beautiful Berkshires region, our knowledgeable team is dedicated to helping you plan the perfect getaway. From luxurious accommodations to exciting outdoor adventures, Berkshires Week offers a wide range of services to ensure a memorable and stress-free vacation. Let us help you explore all that the Berkshires has to offer and create lasting memories in this picturesque destination.

Berkshire East Mountain Resort is a charming lodging destination nestled in the picturesque town of Charlemont, Massachusetts. Situated at 66 Thunder Mountain Road, this resort offers guests a peaceful and serene retreat surrounded by the stunning Berkshire Mountains. With cozy accommodations, breathtaking views, and a range of outdoor activities including skiing, snowboarding, and hiking, Berkshire East Mountain Resort is the perfect destination for those seeking a relaxing getaway in the heart of nature.

Berkshire Trips is a premier travel agency located at 212 Fenn Street in Pittsfield, Massachusetts. We specialize in creating unforgettable experiences in the picturesque Berkshire region of the United States. Our knowledgeable and friendly staff are dedicated to providing top-notch customer service and helping you plan the perfect getaway. Whether you're looking for a relaxing weekend retreat, an adventure-filled outdoor excursion, or a cultural exploration of the area's rich history and arts scene, Berkshire Trips has you covered. Contact us today to start planning your next unforgettable journey in the beautiful Berkshires.

Welcome to Berkshire Hospitality Solutions, your premier destination for exceptional real estate and travel services in the heart of Hancock, Massachusetts. Conveniently located at 31 Madden Road, we specialize in offering personalized solutions for all your property and travel needs. Whether you're looking to buy or sell a property, or seeking the perfect getaway in the picturesque Berkshires, our experienced team is here to guide you every step of the way. With a deep understanding of the local market and a passion for creating memorable travel experiences, Berkshire Hospitality Solutions is dedicated to exceeding your expectations. Explore the best of what Hancock and the surrounding areas have to offer with our tailored services designed just for you. Visit us today and discover how we can turn your real estate dreams and travel aspirations into reality.

Welcome to Berkshire Mobile Home Park, your serene getaway nestled in the heart of the picturesque Berkshires. Conveniently located at 413 Pittsfield Road in Lenox, Massachusetts, our park offers a peaceful retreat for those seeking a unique lodging experience. Whether you're visiting for a weekend escape or an extended stay, you'll find comfort and convenience in our well-maintained facilities. Berkshire Mobile Home Park is not just an RV park; it's a community. We offer spacious lots with full hookups, ensuring you have everything you need for a comfortable stay. Our park is surrounded by the natural beauty of the Berkshires, providing a perfect backdrop for outdoor enthusiasts and nature lovers. Explore nearby hiking trails, enjoy the vibrant local culture, or simply relax and take in the tranquil surroundings.

Welcome to Berkshire Lake Camp, your serene getaway nestled in the heart of the Berkshires at 822 Peru Road, Hinsdale, Massachusetts. Our picturesque camp offers a tranquil escape from the hustle and bustle of everyday life, perfect for families, friends, and solo adventurers seeking a connection with nature. At Berkshire Lake Camp, you'll find a harmonious blend of rustic charm and modern amenities. Our spacious grounds provide ample opportunities for outdoor activities, including hiking, fishing, and kayaking, ensuring there's something for everyone. Enjoy a peaceful afternoon by the lake or explore the nearby trails that showcase the stunning beauty of the Berkshires.

Welcome to New Eatonville Berkshire Spa and Resort, your serene escape nestled in the picturesque town of Lanesborough, Massachusetts. Located at A Street, our resort offers a perfect blend of luxury and tranquility, making it an ideal destination for relaxation and rejuvenation. At New Eatonville Berkshire Spa and Resort, we pride ourselves on providing exceptional lodging experiences that cater to your every need. Our elegantly designed rooms and suites offer breathtaking views of the stunning Berkshire landscape, ensuring a peaceful retreat from the hustle and bustle of everyday life.

Welcome to Anna Fernandez-Gevaert - Best Second Home Realtor in the Berkshires, located at 271 Main Street, Great Barrington, Massachusetts. As a premier real estate expert in the scenic Berkshires region, Anna Fernandez-Gevaert is dedicated to helping you find the perfect second home that suits your lifestyle and needs. With an in-depth knowledge of the local market and a passion for personalized service, Anna provides unparalleled guidance through every step of the buying process. Whether you're seeking a tranquil retreat amidst nature or a charming property in a vibrant community, Anna's expertise and commitment ensure a seamless and rewarding experience. Discover your dream second home in the Berkshires with the trusted assistance of Anna Fernandez-Gevaert. Visit us today and take the first step towards your perfect getaway.

Welcome to Wilder House Berkshires, your serene escape nestled in the heart of the picturesque Berkshires. Located at 48 South Main Street, Sheffield, Massachusetts, our charming lodging offers a perfect blend of comfort, tranquility, and rustic elegance. Whether you're seeking a peaceful retreat or an adventurous getaway, Wilder House provides the ideal base for exploring the natural beauty and cultural richness of the area. Our accommodations are thoughtfully designed to provide a cozy and inviting atmosphere, ensuring a restful stay for all our guests. Each room is equipped with modern amenities while retaining the charm and warmth of a classic Berkshire residence. Wake up to the stunning views of the surrounding landscapes and enjoy a delicious breakfast to start your day.