TOP 30 Best Hiking vacations in Massachusetts

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.

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.

New England Vacation Rentals and Property Management is a premier real estate and travel agency located at 180 Brackett Road in Eastham, Massachusetts. Our expert team specializes in providing top-notch vacation rentals and property management services in the picturesque New England region. Whether you are looking for a cozy beachfront cottage or a luxurious mountain retreat, we have the perfect accommodation for your next getaway. Trust us to handle all your property management needs with professionalism and efficiency. Contact us today to start planning your dream vacation in New England!

Starfish Vacation Village is a charming seaside retreat located at 2032 U.S. 6 in Wellfleet, Massachusetts. Nestled in the heart of Cape Cod, this idyllic resort offers guests a peaceful and relaxing getaway surrounded by natural beauty. The village features cozy cottages, a sparkling swimming pool, and lush gardens, creating the perfect setting for a memorable vacation. Whether you're looking to unwind on the beach, explore the nearby hiking trails, or simply enjoy a quiet evening by the fire pit, Starfish Vacation Village has something for everyone. Come experience the magic of Cape Cod at this hidden gem on the coast.

Dream Vacations is a premier travel agency located at 229 Reed Street in Warren, Massachusetts. With a team of experienced travel experts, we specialize in creating unforgettable vacation experiences for our clients. Whether you're looking for a relaxing beach getaway, an adventurous hiking trip, or a romantic European escape, we have the expertise to make your dream vacation a reality. From booking flights and accommodations to arranging tours and activities, we handle all the details so you can focus on making memories that will last a lifetime. Contact us today to start planning your next dream vacation!

Trailside Cottages at The Mountain Top Inn & Resort offers cozy and charming Vermont vacation homes for rent. Nestled in the picturesque mountains of Cambridge, Massachusetts, these cottages provide the perfect escape for those looking to unwind and reconnect with nature. Whether you're seeking a romantic getaway or a family adventure, our real estate and travel agency team is here to help you find the perfect accommodations for your stay. With breathtaking views and access to a variety of outdoor activities, Trailside Cottages at The Mountain Top Inn & Resort is the ideal destination for your next vacation. Book your stay with us today and experience the beauty of Vermont in comfort and style.

Welcome to Tekoa Park Hiking Trails, a natural oasis nestled in the heart of Russell, Massachusetts. Conveniently located off U.S. 20, our park offers outdoor enthusiasts a serene escape into nature. Whether you're an experienced hiker or just looking for a peaceful walk, our trails cater to all skill levels, winding through lush forests and offering breathtaking views of the surrounding landscape. At Tekoa Park, we are dedicated to preserving the natural beauty of our environment while providing a safe and enjoyable experience for all visitors. Our well-maintained trails are open year-round, allowing you to experience the changing seasons in all their glory. From vibrant spring blooms to the rich hues of autumn leaves, each visit promises a unique and memorable adventure.

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.

Nobnocket Boutique Inn is a chic Martha's Vineyard Hotel located at 60 Mount Aldworth Road in Tisbury, Massachusetts, United States. All rooms at this lodging feature en-suite bathrooms, individually controlled heating and A/C, WiFi, hair-dryers, designer Bluetooth radio/speaker, luxurious Frette linens and towels, Gilchrist & Soames toiletries, Nespresso Coffee machines, TV/DVD, and contemporary ceiling fans. This secluded retreat on 2 acres of gardens offers a unique island experience where guests can enjoy their entire vacation without leaving the property. The modern interior design and expansive outdoor space provide a relaxing escape from the crowds, making it the perfect place for a luxury retreat on Martha's Vineyard. Winner of the prestigious travel award "Best Martha's Vineyard Inn 2019" from Yankee Magazine, this boutique hotel offers tailor-made services for solo, local, and relaxing travelers. Guests can experience summer hiking on Martha's Vineyard at The Brickyard at Menemsha Hills. Come and relax at this refreshingly modern Vineyard Haven Hotel.

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.

Located at 10 MacMillan Pier in Provincetown, Massachusetts, the Schooner Hindu and the Cutter Bloodhound travel agency offers unique and exciting sailing experiences. Step aboard these historic vessels and set sail on the waters of Cape Cod Bay for a memorable adventure. Whether you're looking for a relaxing cruise or a thrilling racing experience, the Schooner Hindu and the Cutter Bloodhound have something for everyone. Book your voyage today and discover the beauty of the Massachusetts coastline from a whole new perspective.

Summer Village on the Pond Westford is a charming lodging institution located at 6 Summer Village Road in Westford, Massachusetts. Nestled in a picturesque setting by a serene pond, this institution offers a peaceful and idyllic retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a perfect home away from home for visitors. With a range of amenities and activities available on-site, including swimming, fishing, and hiking, guests can enjoy a relaxing and rejuvenating stay in the heart of nature. Whether you're looking for a romantic getaway, a family vacation, or a solo retreat, Summer Village on the Pond Westford is the perfect destination for your next trip.

Eddie Jones, Realtor @ Compass is a highly respected institution located at 1100 Massachusetts Avenue in Cambridge, Massachusetts. Eddie is a seasoned real estate professional with a family background in the industry, giving him a wealth of experience from a young age. He is part of the esteemed Currier, Lane, and Young Team and has become a respected figure in the competitive Cambridge/Somerville market over the past four years. Eddie's authentic approach and ability to establish genuine and trustworthy connections with his clients set him apart. Clients feel comfortable, optimistic, and informed every step of the way, thanks to Eddie's attentive and accessible demeanor. He prides himself on providing a no-pressure experience and always safeguards his clients' interests with care and diligence.

Welcome to Shire Village Camp, your ultimate retreat nestled in the picturesque town of Cummington, Massachusetts. Located at 36 Mellor Road, our camp offers a serene escape in the heart of nature, perfect for families, groups, and individuals seeking adventure and relaxation. At Shire Village Camp, we pride ourselves on providing an unforgettable experience that combines the beauty of the great outdoors with comfortable accommodations and a wide array of activities. Whether you're interested in hiking through scenic trails, enjoying a refreshing swim in our pristine lake, or participating in our diverse range of workshops and events, there's something here for everyone.

Welcome to East Rock Inn, your charming getaway nestled in the heart of the Berkshires. Located at 304 State Road, Great Barrington, Massachusetts, our inn offers a perfect blend of comfort and tranquility, making it an ideal destination for both relaxation and adventure. At East Rock Inn, we pride ourselves on providing a warm and inviting atmosphere where guests can unwind and enjoy the natural beauty of the surrounding area. Our elegantly appointed rooms are designed to offer a cozy retreat, complete with modern amenities to ensure a comfortable stay. Whether you're here for a romantic escape, a family vacation, or a solo journey, you'll find the perfect accommodation to suit your needs.

Welcome to Brook Farm Inn, a charming lodging establishment located at 15 Hawthorne Street in Lenox, Massachusetts. Our Victorian Inn offers 15 guest rooms, including a carriage house with three luxury accommodations, perfect for a relaxing getaway in the beautiful Berkshires. Surrounded by trees and award-winning gardens, our inn provides a serene and secluded atmosphere, while still being just a short walk from historic Lenox village. Built in 1882 and furnished with antiques, our elegant inn features a library filled with poetry, history, and literature, where guests can enjoy the soothing sounds of classical music. Each room at Brook Farm Inn includes a full plated breakfast, providing a perfect start to the day before exploring all that the Berkshires have to offer. From skiing and hiking to theater and antiquing, there is something for everyone to enjoy in the area.

Rose and Goat Retreat is a charming and cozy real estate and travel agency located in the picturesque town of North Adams, Massachusetts. Situated at 25 Moores Road, this institution offers a unique blend of services that cater to both property buyers and travelers looking for a peaceful escape. Whether you are in search of a dream home nestled in the scenic beauty of North Adams or planning a relaxing getaway to rejuvenate your soul, Rose and Goat Retreat has got you covered. With a team of experienced professionals and a wide range of properties and travel packages to choose from, you can trust that your needs and preferences will be taken care of with utmost care and attention to detail.

Canterbury Farm is a charming lodging institution located at 1986 Fred Snow Road in Becket, Massachusetts, United States. Surrounded by picturesque countryside, this cozy retreat offers a peaceful escape from the hustle and bustle of city life. Guests can enjoy comfortable accommodations, delicious meals, and a range of outdoor activities such as hiking, fishing, and horseback riding. Whether you're looking for a romantic getaway or a family vacation, Canterbury Farm is the perfect destination for relaxation and rejuvenation.

The Tern Inn is a charming lodging establishment located at 91 Chase Street in the picturesque town of Harwich, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind on Cape Cod. With its convenient location near the beach and local attractions, The Tern Inn is the perfect destination for a peaceful getaway. Enjoy a relaxing stay in this quaint inn and experience true New England hospitality at its finest.

GoshenSummerRentals.com is a vacation property located at 14 West Shore Drive in Goshen, Massachusetts. Run by Dina and her family, the property offers three cozy cottages for rent from June to September. Each cottage is fully equipped with a kitchen, outdoor grill, and private yard. Guests have access to kayaks, canoes, and other water gear, as well as a lakeside firepit. The property is dog-friendly and meticulously cleaned for a safe and enjoyable stay. Nearby attractions include Jacob's Pillow Dance Company, Tanglewood, and the Green River Festival. Guests can also enjoy hiking trails, rafting, and mountain biking in the area. Northampton, a vibrant town with restaurants, shops, and galleries, is just a short drive away. Reviews from previous guests praise the peaceful atmosphere, friendly hosts, and beautiful surroundings of Goshen Summer Rentals. Whether you're looking for a relaxing getaway or an outdoor adventure, this property offers something for everyone.

The Travel Experience Inc. is a premier travel agency located at 634 Broadway in Raynham, Massachusetts, United States. We specialize in creating unforgettable travel experiences for our clients, offering a wide range of services including booking flights, hotels, cruises, and vacation packages. Our team of experienced travel experts is dedicated to providing personalized service and expert advice to help you plan the perfect trip. Whether you're looking for a relaxing beach getaway, an adventurous hiking expedition, or a romantic European escape, The Travel Experience Inc. has you covered. Contact us today to start planning your next unforgettable journey!

AdventureWomen is a renowned travel agency located in Watertown, Massachusetts, United States. Specializing in organizing unforgettable adventures for women of all ages, backgrounds, and interests, AdventureWomen offers a wide range of exciting trips to destinations all over the world. From hiking in the mountains to exploring vibrant cities, each trip is carefully curated to provide a unique and enriching experience for every traveler. With a focus on empowering women through travel, AdventureWomen creates a supportive and inclusive environment for women to step out of their comfort zones, connect with like-minded individuals, and create lasting memories. Whether you're a seasoned traveler or new to the world of adventure, AdventureWomen has the perfect trip for you.

Chang Express is a travel agency located at 192 Broadway in Somerville, Massachusetts. We specialize in providing a wide range of travel services, including booking flights, hotels, car rentals, and vacation packages. Our experienced staff is dedicated to helping our customers plan their dream vacations and create unforgettable travel experiences. Whether you're looking for a relaxing beach getaway, an adventurous hiking trip, or a cultural exploration, Chang Express is here to help you every step of the way. Visit us today to start planning your next adventure!

Welcome to the Appalachian Trail at Lake Buel Rd, a stunning natural haven nestled in the heart of Great Barrington, Massachusetts. As part of the renowned Appalachian National Scenic Trail, this picturesque park offers outdoor enthusiasts a unique opportunity to explore one of the most beautiful sections of the trail. Located at Great Barrington, MA 01230, our park provides visitors with breathtaking vistas, lush forests, and serene landscapes that are perfect for hiking, bird watching, and photography. Whether you're a seasoned hiker or a casual nature lover, the Appalachian Trail at Lake Buel Rd promises an unforgettable experience.

Welcome to Dr. Lisa Lewis Cohasset Family Chiropractic, your trusted partner in achieving optimal health and wellness through natural and effective chiropractic care. Conveniently located at 812 Chief Justice Cushing Highway, Cohasset, Massachusetts, we proudly serve the communities of Cohasset, Hull, Hingham, Scituate, Norwell, and Marshfield. At Cohasset Family Chiropractic, we embrace a unique approach to health that focuses on the body's natural ability to heal itself. Central to our practice is the understanding that a properly functioning nervous system is key to good health. Our expert chiropractic care is designed to ensure that your brain and body communicate effectively, free from any interference caused by vertebral subluxations.

The Lamb and Lion Inn, located at 2504 Main Street in Barnstable, Massachusetts, is a classic Cape Cod inn with the spirit of a small luxury hotel. It has been recognized as one of the top 12 pet-friendly properties in the world, making it the perfect destination for travelers with furry friends. The inn offers ultimate guest privacy with multiple separate entrances and exits, ensuring a peaceful and relaxing stay. Situated on 4 acres in historic Cape Cod Bay, the inn is just minutes away from Barnstable Village's shops, restaurants, waterfront dining, and whale watch boat. Guests can also enjoy a short walk to a sunset beach and hiking trails, as well as a ten-minute drive to the island ferries and Hyannis' nightlife. The inn dates back to a 1740 farmhouse with horse stables that have been converted into suites, and features the original 1740 Barn and a central courtyard for a fun and relaxed atmosphere.

Kingfisher Lodging is a pet-friendly accommodation located at 177 Main Street in Dennis, Massachusetts. Since 2001, the Fisher family has been welcoming guests to this historic property on Cape Cod. The recently renovated motel is just a short drive from some of the finest beaches, restaurants, and attractions in the area. Guests can relax at the outdoor pool, one of the largest in the region, or take their four-legged friend to the fenced-in dog run. The hotel prides itself on being one of the few pet-friendly options on Cape Cod.

Welcome to Pleasant Kennels, located at 1009 Pleasant Street in Leominster, Massachusetts! At Pleasant Kennels, we offer a comfortable and welcoming environment for your furry family member. Our facility is equipped with heating and air conditioning to ensure a pleasant stay for your dog, whether they are with us for a day, a week, or longer. We provide indoor and outdoor access all day long, structured playgroups, and hikes for your pet's enjoyment. Whether you need daily care while you're at work or away, or are looking for a boarding facility for your pup while you're on vacation, Pleasant Kennels has you covered.

Vicky's Travel Services Inc is a reputable travel agency located at 695 Washington Street in Attleboro, Massachusetts, United States. With a team of experienced travel experts, we specialize in providing personalized travel solutions for all your vacation needs. Whether you're looking to book a relaxing beach getaway, an adventurous hiking trip, or a romantic European tour, we are here to help you plan the perfect itinerary. Contact us today to start planning your dream vacation with Vicky's Travel Services Inc.

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.