TOP 30 Berkshires getaway in Massachusetts

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Welcome to Berkshire Hathaway HomeServices - Realty Professionals - Otis Office, your trusted real estate partner located at 48 East Otis Road, Otis, Massachusetts. Nestled in the heart of the Berkshires, our agency is dedicated to providing exceptional real estate services to buyers and sellers throughout the region. Whether you're searching for your dream home, a vacation getaway, or looking to sell your property, our team of experienced professionals is here to guide you every step of the way. At Berkshire Hathaway HomeServices - Realty Professionals, we pride ourselves on our in-depth local knowledge and commitment to customer satisfaction. Our agents are well-versed in the unique charm and opportunities that the Otis area offers, ensuring that you receive personalized and insightful advice tailored to your needs. We offer a comprehensive range of services, including residential sales, property listings, market analysis, and more.

Field Farm Reservation is a park and tourist attraction located at 554 Sloan Road, Williamstown, Massachusetts, United States. It is known as Williamstown’s favorite authentic mid-century modern B&B and has been rated #1 Bed & Breakfast in Williamstown, MA by Tripadvisor. The institution offers a unique experience with two Modernist homes, including a bed & breakfast, and over 300 acres of open fields, woods, and wetlands with four miles of footpaths. Guests can enjoy a peaceful getaway vacation in the Berkshires or explore beautiful sculptures and architecture at Field Farm. The Guest House at Field Farm is an architectural gem offering authentic mid-century-modern accommodations with stunning views of Mt. Greylock. The property also features period artwork and thirteen sculptures in the surrounding gardens. Visitors can explore the property or stay in The Folly, a three-bedroom guest cottage designed by modernist architect Ulrich Franzen in 1965. Field Farm offers special winter discounts for guests staying between November 20, 2023, and March 11, 2024. The institution provides opportunities for outdoor activities such as walking, snowshoeing, and cross-country skiing on its 320-acre property. Guests can also enjoy hiking on more than four miles of trails with scenic views of Mount Greylock. The property is home to a variety of wildlife, including white-tail deer, coyotes, bobcats, beavers, turtles, and various bird species. The Guest House at Field Farm offers six spacious and finely appointed rooms with mountain views, although the facility is not wheelchair accessible. Visitors can use the electric car charger for overnight guests staying at the Field Farm Inn. The property also hosts private events and groups, and guests are encouraged to take a photo of the map or download a trail map before heading out. Field Farm is part of The Trustees, an organization dedicated to preserving and protecting Massachusetts’ special places. The institution offers a unique blend of history, architecture, design, and natural beauty, making it a must-visit destination for a weekend trip or a cozy inn stay.

White Glove Travel Service is a premier travel agency located at 81 Berkshire Road in Needham, Massachusetts. With a reputation for providing top-notch service and personalized attention to detail, our team of experienced travel experts is dedicated to creating unforgettable travel experiences for our clients. Whether you're looking to book a luxury vacation, a romantic getaway, or a corporate retreat, we are committed to going above and beyond to ensure that every aspect of your trip is seamless and stress-free. Contact us today to start planning your next adventure with White Glove Travel Service.

Welcome to Bob's Way, a serene haven nestled in the heart of Monterey, Massachusetts. As a premier park destination in the picturesque Berkshires, Bob's Way offers an idyllic escape for nature lovers and outdoor enthusiasts alike. Immerse yourself in the tranquility of lush landscapes, winding trails, and breathtaking vistas that define our unique park. Whether you're seeking a peaceful stroll, a challenging hike, or a perfect picnic spot, Bob's Way caters to all. Our well-maintained paths invite you to explore the natural beauty of the region, while our scenic overlooks provide stunning views that capture the essence of New England's charm. Families, friends, and solo adventurers will find plenty of spaces to relax, play, and connect with nature.

Race Brook Lodge is a charming institution nestled in the beautiful countryside of Sheffield, Massachusetts. Located at 864 South Undermountain Road, this unique establishment offers a blend of health, lodging, and park amenities for guests to enjoy. From cozy accommodations to wellness retreats, Race Brook Lodge provides a tranquil escape from the hustle and bustle of everyday life. Explore the lush surroundings, unwind in the peaceful atmosphere, and rejuvenate your mind, body, and soul at this idyllic retreat in the heart of the Berkshires.

Sheffield Lodge is a charming lodging located at 400 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to escape the hustle and bustle of city life. Whether you're seeking a romantic getaway or a relaxing vacation in nature, Sheffield Lodge provides a tranquil setting for all guests to unwind and rejuvenate. With its convenient location near local attractions and outdoor activities, this institution is the perfect destination for those seeking a peaceful retreat in the heart of Massachusetts.

The Inn at Freeman Elms Farm B&B is a charming and welcoming lodging establishment located in the picturesque town of New Marlborough, Massachusetts. Situated at 566 Mill River Great Barrington Road, this historic bed and breakfast offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by the natural beauty of the Berkshires, the Inn at Freeman Elms Farm B&B provides a cozy and comfortable atmosphere for guests to unwind and recharge. The property boasts beautifully appointed rooms, each uniquely decorated to provide a home away from home experience. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients.

Birch Hill Bed & Breakfast is a charming lodging located at 254 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshires region, this cozy B&B offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. With comfortable accommodations, delicious homemade breakfasts, and warm hospitality, Birch Hill Bed & Breakfast is the perfect place to relax and unwind during your stay in the Berkshires.

Welcome to Monument Mountain Motel, a budget-friendly lodging option in the heart of Great Barrington, Massachusetts. Located in the beautiful Berkshire Mountains, our motel offers comfortable rooms and family-style amenities. Whether you're in town for business or pleasure, our convenient location puts you near iconic attractions such as Tanglewood Music Festival, Ski Butternut Resort, and the Norman Rockwell Museum. At Monument Mountain Motel, we strive to provide a pleasant and affordable experience for all our guests. Enjoy free wifi, in-room microwaves and fridges, and a spacious patio with barbecue facilities. Family travelers will appreciate our family-friendly amenities, while business travelers will find our simplicity and affordability to be just what they need.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

The Barrington Bed and Breakfast is a charming lodging establishment located at 281 Main Street in the picturesque town of Great Barrington, Massachusetts. This cozy B&B offers a warm and inviting atmosphere for guests looking for a relaxing getaway in the heart of the Berkshires. The beautifully decorated rooms are equipped with modern amenities to ensure a comfortable stay, and guests can enjoy a delicious homemade breakfast each morning. Conveniently located near shops, restaurants, and attractions, The Barrington Bed and Breakfast is the perfect choice for those seeking a peaceful retreat in a quaint New England town.

Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.

The Egremont Village Inn is a charming and historic lodging establishment located at 17 Main Street in the picturesque town of Egremont, Massachusetts, United States. This cozy inn offers a comfortable and welcoming atmosphere, perfect for a relaxing getaway in the Berkshires. Guests can enjoy beautifully appointed rooms, delicious meals at the on-site restaurant, and easy access to the area's many attractions and outdoor activities. Whether you're looking for a romantic retreat, a family vacation, or a solo adventure, The Egremont Village Inn is the perfect choice for your stay in the Berkshires.

Granville House is a charming lodging institution located at 98 Division Street in the picturesque town of New Marlborough, Massachusetts. This cozy and inviting establishment offers comfortable accommodations for visitors looking to experience the beauty and tranquility of the Berkshires region. With its convenient location and warm hospitality, Granville House is the perfect choice for a relaxing getaway in New England.

Located in the quaint village of New Marlborough in Massachusetts, The Old Inn On The Green is a historic institution offering both bar services and lodging. The inn, originally a stagecoach relay, features beautifully restored guest rooms, fine dining in candlelit rooms, and seasonal outdoor dining on the garden terrace. The Southfield Store, open for takeout daily, is also part of the institution. Whether you are visiting for business or pleasure, for dinner or an overnight stay, The Old Inn On The Green provides a charming and authentic experience in the heart of the Berkshire region. With its picturesque surroundings of rolling fields and meadows, this historic inn is a perfect destination for those seeking a peaceful retreat in New England. Visit us at 134 Hartsville-New Marlborough Rd, New Marlborough, MA 01230 or contact us at 413-229-7924 or info@oldinn.com. Feel the love and experience the best of the oldest at The Old Inn On The Green.

Maplewood Bed & Breakfast is a charming lodging establishment located at 266 Massachusetts 8 North in Otis, Massachusetts, United States. Nestled in a picturesque setting, this cozy bed and breakfast offers guests a peaceful retreat surrounded by nature. The comfortable accommodations and warm hospitality make Maplewood Bed & Breakfast the perfect choice for a relaxing getaway in the beautiful Berkshires region. With its convenient location and inviting atmosphere, guests can enjoy a memorable stay at this delightful B&B.

Located in the picturesque town of Sandisfield, Massachusetts, Hillside Garden Inn offers a charming and relaxing Bed and Breakfast experience. Housed in the historic Elijah Twining House, dating back to 1785, guests can enjoy immaculate accommodations and gracious hospitality. The inn boasts a spacious wrap-around porch overlooking the Farmington River, as well as a screened-in patio and hilltop gazebo with stunning panoramic views of the distant hills. Sandisfield, with its beautiful landscapes and thriving arts scene, is the perfect destination for outdoor enthusiasts and culture lovers alike. The Berkshires region offers plenty of activities year-round, from skiing and hiking to water sports and cultural events. For those who enjoy shopping, Prime Outlets are just a short drive away.

Briarcliff Motel is a charming lodging establishment located at 506 Stockbridge Road in Great Barrington, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beauty of the region. With its convenient location and friendly staff, Briarcliff Motel is the perfect choice for a relaxing getaway in the heart of New England.

Brook Cove is a charming lodging institution located at 30 Linda Lane in the picturesque town of Great Barrington, Massachusetts. Surrounded by lush greenery and peaceful surroundings, Brook Cove offers a serene retreat for guests looking to escape the hustle and bustle of city life. The cozy accommodations and warm hospitality make it the perfect destination for a relaxing getaway. Whether you're looking to explore the beautiful Berkshires or simply unwind in nature, Brook Cove provides a tranquil and comfortable stay for all visitors.

TOURISTS is a unique lodging institution located at 915 State Road in North Adams, Massachusetts. Situated in the scenic Berkshires region of the United States, TOURISTS offers a one-of-a-kind experience for travelers looking to immerse themselves in nature and art. The institution provides a range of accommodations, from cozy cabins to stylish rooms, all designed with a modern and minimalist aesthetic. Guests can enjoy amenities such as a communal kitchen, outdoor fire pits, and access to hiking trails. Whether you're seeking a peaceful retreat or a cultural adventure, TOURISTS is the perfect destination for your next getaway.

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

Manor Lane is a charming institution located at 145 Hurlburt Road in Great Barrington, Massachusetts. This real estate and travel agency offers a unique rental home with French elegance in the tranquil Berkshire mountains. The private 4 bedroom, 4 bath home is the perfect vacation rental, just 5 minutes away from the town of Great Barrington. Escape to this one-of-a-kind Berkshire vacation rental for a summer getaway or holiday retreat. Immerse yourself in the beauty of the Berkshire mountains while enjoying all that Great Barrington has to offer. Experience the best of both worlds at Manor Lane, where luxury meets relaxation in the heart of Massachusetts.

The Red House on Lake Buel is a charming Berkshire lakeside cottage offering a peaceful retreat for those seeking relaxation and outdoor activities. Located at 24 Downs Road in New Marlborough, Massachusetts, this vacation rental property is just a short distance from popular attractions such as Tanglewood, Jacobs Pillow, Norman Rockwell Museum, and Chesterwood. This idyllic 4 bedroom cottage is situated right on the edge of Lake Buel, providing easy access to swimming, fishing, water sports, and hiking. The house features a spacious screened-in porch with comfortable seating and a dining table for 8, perfect for enjoying meals with a view of the lake. Guests can also bring their own boat and dock it at the private dock.

Benton Cove Cabins is a real estate and travel agency located at 189 Ray Hubbard Road in Otis, Massachusetts, United States. Our lakeside cabin rental, "Leeway," offers stunning sunsets and a peaceful retreat on Benton Pond. The 2024 season runs from May 17 to October 13, offering activities such as hiking, swimming, canoeing, kayaking, and more. "Leeway" comfortably sleeps six guests and features two bedrooms, a fully equipped kitchen, a bathroom with modern amenities, and a cozy living room with a stone fireplace. Guests can enjoy their private dock, gas grill, and access to row boats, a canoe, and kayaks. With 225 feet of lakefront shared with our sister cabin "Arcadia," Benton Cove Cabins is the perfect destination for families seeking a relaxing getaway in the Berkshires.

Mount Everett State Reservation is a picturesque park and tourist attraction located at 143 East Street in Mount Washington, Massachusetts, United States. This stunning natural oasis offers visitors the opportunity to explore lush forests, scenic hiking trails, and breathtaking mountain views. Whether you're looking for a peaceful escape into nature or an exciting outdoor adventure, Mount Everett State Reservation has something for everyone to enjoy. Come and experience the beauty of this hidden gem in the heart of the Berkshires.

Camp Timber Trails is a stunning outdoor venue located at 1266 East Otis Road, Tolland, Massachusetts, United States. Situated on 417 acres of secluded forest in the Berkshires foothills, this institution offers a serene setting for retreats, reunions, weddings, and special events. The private lake with its own island adds to the charm of the location. CTT provides ample facilities for various camps and educational programs, making it an ideal destination for those looking to connect with the natural world. The institution expresses gratitude to the Mass Cultural Council for their generous support.

The Inn At Richmond is a charming lodging establishment located at 802 State Road in the picturesque town of Richmond, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic inn offers a peaceful retreat for guests seeking a relaxing getaway. With cozy rooms, elegant decor, and modern amenities, The Inn At Richmond provides a comfortable and inviting atmosphere for visitors to enjoy. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution is the perfect choice for your stay in the Berkshires.

Located at 10 Richmond Mountain Road in Lenox, Massachusetts, the Apple Tree Inn is a charming lodging option that serves as the perfect retreat for those looking to nurture their creativity. Surrounded by the natural beauty of the Berkshires, this institution offers a peaceful escape from the ordinary where guests can unlock new ideas and inspiration. The inn features a picturesque 1885 Victorian main house with 13 rooms that blend historic charm with modern amenities such as Frette linens. Additionally, there is a rustic Lodge with 21 rooms that provide a cozy and tranquil setting overlooking the lush green forests and rolling hills of the Berkshires.

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

Located in the charming town of Lenox, Massachusetts, the Eastgate Inn Bed & Breakfast offers a cozy and welcoming atmosphere for travelers looking for a peaceful retreat. Situated at 207 West Street, this quaint lodging establishment provides comfortable accommodations with a personal touch. Guests can enjoy a delicious homemade breakfast each morning before exploring the nearby attractions such as Tanglewood, The Mount, and the shops and restaurants of Lenox. Whether you are visiting for a romantic getaway or a relaxing vacation, the Eastgate Inn Bed & Breakfast is the perfect place to stay in the heart of the Berkshires.