TOP 30 Berkshires vacation spots in Massachusetts

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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.

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.

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.

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.

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.

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.

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.

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.

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.

Becket Quarry is a picturesque park and tourist attraction located at 456 Quarry Road in Becket, Massachusetts, United States. This historic site offers visitors the opportunity to explore the remnants of an old quarry, with stunning rock formations and crystal-clear water. Perfect for hiking, picnicking, and photography, Becket Quarry is a must-visit destination for nature lovers and history enthusiasts alike. Immerse yourself in the natural beauty and unique charm of this hidden gem in the heart of the Berkshires.

The Trail in Adams is a charming lodging and store located at 10 Pleasant Street in Adams, Massachusetts. This cozy establishment offers comfortable accommodations for travelers exploring the beautiful Berkshire region. Guests can also browse through the store's selection of unique gifts, local crafts, and outdoor gear. Whether you're looking for a place to rest after a day of hiking or shopping for a special souvenir, The Trail in Adams is the perfect destination for your next adventure.

Walker House is a historic institution located at 64 Walker Street in the charming town of Lenox, Massachusetts. This elegant building offers a unique blend of traditional charm and modern amenities, making it the perfect destination for visitors looking to experience the beauty of the Berkshires. With its picturesque surroundings and convenient location, Walker House is the ideal spot for a relaxing getaway or a special event. Immerse yourself in the rich history and warm hospitality of this iconic institution during your stay in Lenox.

Mount Greylock State Reservation is a stunning natural oasis located at 30 Rockwell Road in Lanesborough, Massachusetts. This institution offers a variety of amenities including a campground, lodging facilities, and a beautiful park for visitors to explore and enjoy. As the highest point in Massachusetts, Mount Greylock State Reservation is a popular tourist attraction for outdoor enthusiasts looking to hike, camp, or simply take in the breathtaking views of the surrounding landscape. Whether you're seeking a peaceful retreat in nature or an exciting adventure, Mount Greylock State Reservation has something for everyone to enjoy.

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.

Moore State Park, located at 1 Sawmill Road in Paxton, Massachusetts, is a picturesque park and popular tourist attraction. This beautiful park offers visitors a peaceful escape into nature with its lush greenery, tranquil ponds, and scenic walking trails. Visitors can enjoy picnicking, hiking, fishing, and birdwatching in this serene setting. Moore State Park is the perfect destination for a relaxing day outdoors with family and friends, or for solo exploration and reflection. Whether you're looking for a leisurely stroll or a more active outdoor adventure, Moore State Park has something for everyone to enjoy.

Welcome to Partridge Hollow Campground, your serene getaway nestled in the beautiful landscape of West Stockbridge, Massachusetts. Located at 5 Albany Road, our campground offers a perfect blend of nature and comfort, making it an ideal destination for families, couples, and outdoor enthusiasts seeking a memorable retreat. At Partridge Hollow Campground, we pride ourselves on providing a welcoming and relaxing environment for all our guests. Our spacious campsites are designed to accommodate tents, RVs, and trailers, ensuring that everyone can enjoy the great outdoors in their preferred style. Each site is equipped with essential amenities to make your stay as comfortable as possible.

Welcome to The Trustees of Reservations, a haven for nature lovers and history enthusiasts alike, located at 1 Sergeant Street, Stockbridge, Massachusetts. As a distinguished museum and tourist attraction, we are dedicated to preserving the exceptional scenic, historic, and ecological treasures of Massachusetts. Our mission is to protect the places you love for their trails, history, gardens, and beaches, recognizing that nature and culture enrich our lives and soothe the soul. Explore the beauty of Massachusetts through our diverse offerings, from historic estates to breathtaking natural landscapes. Immerse yourself in our scenic trails, picturesque gardens, and serene beaches that promise a rejuvenating experience. For those interested in history, delve into the rich past of the region with guided tours and educational programs.

Welcome to Carriage House, a charming haven nestled in the picturesque town of Stockbridge, Massachusetts. Located in the heart of the Berkshires at 01240, our establishment offers a unique blend of historic charm and modern comfort, making it the perfect destination for both locals and visitors alike. At Carriage House, we pride ourselves on providing an exceptional experience that caters to a variety of needs. Whether you're seeking a cozy retreat, a venue for special occasions, or a delightful spot to unwind, our welcoming atmosphere and attentive service ensure a memorable visit. Our beautifully appointed spaces reflect the rich history of Stockbridge while offering all the contemporary amenities you desire.

Welcome to Camp Arrow Wood, your premier destination for outdoor adventure and relaxation in the heart of the Berkshires! Nestled at 195 Cloverdale Street, Pittsfield, Massachusetts, our camp offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a weekend getaway, a summer retreat, or a place to connect with nature, Camp Arrow Wood is the perfect spot. Our beautiful grounds boast a variety of amenities and activities for all ages. Explore our extensive hiking trails, enjoy a leisurely paddle on our scenic lake, or challenge yourself with our ropes course and climbing wall. For those looking to unwind, our tranquil setting provides the ideal backdrop for meditation, yoga, or simply soaking in the natural beauty.

Welcome to Bear Mountain, a serene and picturesque park nestled in the heart of the Berkshires at 69 Blue Hill Road, Monterey, Massachusetts. Our park offers a tranquil escape from the hustle and bustle of everyday life, inviting visitors to immerse themselves in the natural beauty of the region. Bear Mountain is a haven for outdoor enthusiasts and families alike, offering a variety of recreational activities throughout the year. Explore our scenic hiking trails that wind through lush forests and offer breathtaking views of the surrounding landscape. In the warmer months, enjoy picnicking in our well-maintained areas or embark on a bird-watching adventure to spot some of Massachusetts' native wildlife.

Welcome to Haley Brook Falls, your serene escape nestled in the heart of Williamstown, Massachusetts. Located in the picturesque Berkshires, our charming establishment offers a tranquil retreat for nature lovers and adventure seekers alike. Haley Brook Falls is not just a destination, but an experience that rejuvenates the soul and invigorates the senses. Our beautiful property is surrounded by lush forests and cascading waterfalls, providing the perfect backdrop for a relaxing getaway. Whether you're here to explore the local hiking trails, enjoy a peaceful picnic by the falls, or simply unwind in nature's embrace, Haley Brook Falls offers something for everyone.

Welcome to Rockwell Pond, a serene oasis nestled in the heart of Williamstown, Massachusetts. As a premier tourist attraction in the picturesque Berkshires, Rockwell Pond offers visitors a tranquil escape from the hustle and bustle of everyday life. Surrounded by lush greenery and vibrant wildlife, this charming spot invites you to unwind and connect with nature. Whether you're an avid birdwatcher, a photography enthusiast, or simply seeking a peaceful retreat, Rockwell Pond provides the perfect setting. Stroll along the scenic walking paths, enjoy a leisurely picnic by the water's edge, or take in the breathtaking views that change with the seasons. Our pond is also a haven for fishing enthusiasts, offering a delightful experience for both beginners and seasoned anglers.

Welcome to the Appalachian Trail at Housatonic St, a serene park located at 470-494 West Housatonic Street in the picturesque town of Dalton, Massachusetts. Nestled amidst the natural beauty of the Berkshires, this section of the iconic Appalachian Trail offers a peaceful retreat for nature enthusiasts, hikers, and families alike. Explore miles of well-maintained trails that wind through lush forests, open meadows, and along the tranquil Housatonic River. Whether you're embarking on a challenging hike or enjoying a leisurely stroll, the park provides breathtaking vistas and a chance to reconnect with nature. This location is perfect for spotting local wildlife, capturing stunning photographs, or simply unwinding in a serene environment.

Welcome to Peck's Falls, a hidden gem nestled in the heart of Adams, Massachusetts. Located in the picturesque Berkshires, our charming establishment offers a perfect blend of natural beauty and local hospitality. Whether you're a nature enthusiast or simply seeking a tranquil escape, Peck's Falls is the ideal destination. Situated at the address Adams, Massachusetts 01220, Peck's Falls provides easy access to breathtaking waterfalls and scenic trails that capture the essence of New England's landscape. Our location is perfect for outdoor adventures, with opportunities for hiking, picnicking, and photography.

Welcome to Mountain View Campground, your serene escape nestled in the heart of the Berkshires at 1856 South Main Road, Otis, Massachusetts. Our picturesque campground offers a perfect blend of natural beauty and modern amenities, ideal for families, solo travelers, and adventure seekers alike. Surrounded by lush forests and stunning mountain vistas, Mountain View Campground provides a tranquil setting for your outdoor getaway. Whether you're pitching a tent, parking your RV, or staying in one of our cozy cabins, you'll find comfort and convenience in every corner of our well-maintained facilities. Enjoy a variety of recreational activities, from hiking and fishing to stargazing and campfire storytelling, making each stay a memorable adventure.

Welcome to Lakeview Orchard, your go-to destination for fresh, locally-grown produce nestled in the heart of the Berkshires at 94 Old Cheshire Road, Lanesborough, Massachusetts. Our family-owned orchard offers a picturesque setting where visitors can enjoy the beauty of nature while picking their own apples, peaches, and berries during the harvest seasons. At Lakeview Orchard, we pride ourselves on sustainable farming practices, ensuring that our produce is not only delicious but also environmentally friendly. Our farm store features a delightful selection of homemade jams, cider, and baked goods, all crafted with love and the finest ingredients.

Welcome to Dayville Trailhead, your gateway to outdoor adventure in the heart of Chester, Massachusetts. Nestled in the scenic landscapes of the Berkshires, our park offers nature enthusiasts a perfect escape into the tranquility of the great outdoors. Whether you're an avid hiker, a casual walker, or simply looking to enjoy a peaceful picnic, Dayville Trailhead provides the ideal setting for all your recreational needs. Explore our well-maintained trails that wind through lush forests, offering breathtaking views and the chance to observe local wildlife in their natural habitat. Our park is designed to cater to all skill levels, ensuring a safe and enjoyable experience for families, solo adventurers, and groups alike.

Welcome to Cold River Bend, a charming local haven nestled in the heart of Savoy, Massachusetts. Located at 386 Massachusetts Route 2, our establishment offers a serene escape surrounded by the natural beauty of the Berkshires. Cold River Bend is more than just a destination; it's an experience that captures the essence of New England's rustic charm. Whether you're a local resident or a traveler passing through, you'll find a warm welcome and a variety of offerings to suit your needs. Our inviting atmosphere and friendly service make Cold River Bend the perfect spot for relaxation and enjoyment. Discover a unique blend of local products, handcrafted goods, and delightful treats that celebrate the rich heritage and community spirit of the area.

Welcome to Suzanne Crerar at Stone House Properties, your premier real estate partner located at 38 Main Street, West Stockbridge, Massachusetts. Serving the beautiful regions of Berkshire County, Massachusetts, and Columbia County, New York's Upper Hudson Valley, we are a well-established brokerage firm dedicated to providing exceptional services for both buyers and sellers. Our region is renowned for its breathtaking natural beauty, with the Berkshires and Upper Hudson Valley offering picturesque landscapes of rolling hills and expansive valleys. In addition to the stunning scenery, our area is rich in cultural landmarks, including Tanglewood, MASS MoCA, and the Olana State Historic Site, making it a truly desirable location for your next home.