TOP 30 Berkshire mountains vacation in Massachusetts

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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 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.

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.

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.

Jiminy Peak Mountain Resort is a premier destination located at 37 Corey Road in Hancock, Massachusetts, United States. This institution offers a wide range of activities for visitors, including skiing and snowboarding in the winter, as well as hiking, biking, and zip-lining in the summer. With on-site lodging options, dining establishments, and a variety of recreational amenities, Jiminy Peak Mountain Resort is the perfect destination for a family vacation or weekend getaway. Experience the beauty of the Berkshire Mountains while enjoying all that this top-rated tourist attraction has to offer.

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.

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 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.

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.

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.

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.

Welcome to Quality Inn Great Barrington, a 100% smoke-free hotel located at 372 Main Street in the charming forested mountain town of Great Barrington, Massachusetts. Whether you are visiting for business or pleasure, our hotel offers excellent value and a range of amenities to ensure a great experience during your stay. Our hotel features free wifi throughout the property, a complimentary continental breakfast each morning, free parking, an exercise room, and 24-hour desk service. Each room is equipped with a fridge, microwave, flat-screen television, desk with chair, coffee maker, and more. We strive to provide all the amenities you expect, along with special touches to enhance your Berkshires experience.

Laurel Ridge Campground is a family-friendly destination located in the picturesque Berkshire mountains of Otis, Massachusetts. Whether you're camping solo or with a group, our campground offers a variety of sites to suit your needs. From grassy safari field sites to gravel or grass inner loop sites, there's something for everyone. Our campground features a range of amenities, including a new playscape for kids, a basketball court, horseshoes, a swimming pool, and even bingo nights. If you're looking for a peaceful retreat, you'll find plenty of relaxation here too. Enjoy the fresh mountain air, good company, and a full schedule of activities to keep you entertained.

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.

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.

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.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Bascom Lodge is a charming lodging institution nestled in the picturesque surroundings of Adams, Massachusetts. Located at 3 Summit Road, this historic lodge offers guests a unique and tranquil retreat in the heart of the Berkshires. With cozy accommodations and stunning views of the surrounding mountains, Bascom Lodge is the perfect destination for nature lovers and outdoor enthusiasts. Whether you're looking to relax and unwind or explore the nearby hiking trails and attractions, Bascom Lodge provides a comfortable and welcoming atmosphere for all guests. Experience the beauty and serenity of the Berkshires at Bascom Lodge.

Historic Valley Campground is a charming and picturesque campground located at 200 Windsor Lake Road in North Adams, Massachusetts. Nestled in the beautiful Berkshire Mountains, this campground offers a peaceful and serene setting for visitors to relax and unwind. With a variety of lodging options, including tent sites and cabins, guests can enjoy a comfortable stay surrounded by nature. The campground also features a park area with walking trails, picnic areas, and a scenic lake for fishing and boating. Whether you're looking for a weekend getaway or a longer vacation, Historic Valley Campground is the perfect destination for outdoor enthusiasts and nature lovers alike.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

Blue Vista Motor Lodge is a charming lodging establishment located at 229 Mohawk Trail in the picturesque town of Florida, Massachusetts. Surrounded by the stunning natural beauty of the Berkshires, this cozy lodge offers comfortable accommodations and a warm, welcoming atmosphere. Whether you are passing through on a road trip or looking for a peaceful retreat in the mountains, Blue Vista Motor Lodge is the perfect place to rest and recharge. With friendly staff, clean rooms, and convenient amenities, your stay at Blue Vista Motor Lodge is sure to be a relaxing and enjoyable experience.

Foolhardy Hill is a charming campground, lodging, and park located at 232 Zoar Road in the picturesque town of Charlemont, Massachusetts, United States. Nestled in the rolling hills of the Berkshires, this institution offers a one-of-a-kind experience for nature lovers and outdoor enthusiasts. With spacious campsites, cozy cabins, and a variety of recreational activities, including hiking, fishing, and birdwatching, Foolhardy Hill provides the perfect getaway for those looking to unwind and reconnect with the great outdoors. Whether you're seeking a peaceful retreat or an action-packed adventure, this hidden gem is sure to delight visitors of all ages.

Upper Goose Pond Cabin is a charming wilderness retreat nestled in the heart of Lee, Massachusetts. This rustic lodging offers a tranquil escape from the hustle and bustle of city life, surrounded by the natural beauty of the Berkshire Mountains. The cabin is located right on the shores of Upper Goose Pond, providing guests with stunning views and opportunities for fishing, swimming, and hiking. Whether you're looking for a peaceful weekend getaway or a basecamp for outdoor adventures, Upper Goose Pond Cabin is the perfect destination.

Privacy Campground, nestled against Brodie Mountain in the picturesque Berkshires of Massachusetts, offers a peaceful retreat beneath the stars. Located just south of Williamstown, this family-owned campground provides a perfect setting for outdoor adventures and relaxation. Established in 1973, Privacy Campground has been a beloved destination for generations of families. From the well-maintained facilities to the scenic walking trails, every aspect of the campground is designed to bring families together in a shared sense of community.

Nestled in the picturesque town of Charlemont, Massachusetts, Mohawk Trail State Forest offers a tranquil escape into nature. This campground, lodging, and park is the perfect destination for outdoor enthusiasts looking to explore the beauty of the Berkshire Mountains. With over 6,000 acres of pristine wilderness to explore, visitors can enjoy hiking, fishing, and camping in a serene and peaceful setting. The Cold River Road location provides easy access to the forest's many trails and scenic overlooks, making it an ideal spot for a weekend getaway or a longer vacation. Whether you're looking to relax in a cozy cabin, pitch a tent under the stars, or simply unwind in the great outdoors, Mohawk Trail State Forest has something for everyone.