TOP 30 Best Families on vacation in Massachusetts

s most beautiful estates, Castle Hill on the Crane Estate in Ipswich, Massachusetts. Explore the grandeur of this historic seaside estate, with its beautifully landscaped grounds, restored Grand Allée, gardens, and Casino complex. Originally stewarded by indigenous peoples, Castle Hill has a deep and storied past dating back to the 1600s. The estate was transformed into one of America's great Country Place Era estates by Chicago industrialist Richard Teller Crane Jr. and his wife Florence Higinbotham Crane in the early 1900s.

The Boston Center for Youth & Families (BCYF) is located at 1483 Tremont Street in Boston, Massachusetts, United States. As the City of Boston's largest human service agency, BCYF manages over 30 facilities, including community centers and pools, all of which are dedicated to enhancing the quality of life for Boston's residents. Our mission is to partner with organizations to offer a wide range of programs and activities tailored to neighborhood needs and interests. At BCYF, we offer affordable programs for all ages at our 36 facilities throughout Boston. Our Adult Education Programming helps individuals build essential life and work skills, while our City Hall Childcare Program provides nurturing and affordable care for children. Our G.I.R.L.S. programs focus on Growth, Intervention, Respect, Leadership, and Service for girls, and our Senior Programs cater to older adults in BCYF centers and standalone senior centers.

Property Cape Cod Vacation Rentals is a premier real estate and travel agency located in the heart of Barnstable, Massachusetts. We specialize in providing top-notch vacation rental properties on the beautiful Cape Cod peninsula. Our dedicated team of professionals is committed to helping you find the perfect rental for your next getaway, whether you're looking for a cozy beach cottage or a luxurious waterfront estate. With our extensive knowledge of the area and personalized service, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream Cape Cod vacation!

The Inn on Main is a charming lodging establishment located on Massachusetts 6A in Yarmouth, Massachusetts. This cozy inn offers a comfortable and welcoming atmosphere for guests to relax and unwind during their stay. With its convenient location in the heart of Yarmouth, guests can easily explore the nearby attractions, shops, and restaurants. The Inn on Main provides well-appointed rooms, friendly staff, and top-notch amenities to ensure a memorable and enjoyable experience for all visitors. Whether you are in town for a weekend getaway or a business trip, the Inn on Main is the perfect place to call home while in Yarmouth.

Simple Family Travel is a premier travel agency located at 44A Cloutmans Lane in Marblehead, Massachusetts. Our agency specializes in creating unforgettable family vacations that are stress-free and tailored to your specific needs. Whether you're looking for a relaxing beach getaway, a fun-filled theme park adventure, or a cultural exploration, our team of experienced travel experts will work with you to plan the perfect trip for your family. Let us take the hassle out of vacation planning so you can focus on making memories that will last a lifetime. Contact us today to start planning your next family adventure!

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.

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.

On Cranberry Pond Bed & Breakfast is a charming lodging establishment located at 43 Fuller Street in Middleborough, Massachusetts. Situated on the picturesque Cranberry Pond, guests can enjoy a peaceful and relaxing stay in the heart of nature. The cozy rooms are tastefully decorated and offer all the comforts of home. Guests can start their day with a delicious homemade breakfast served in the dining area overlooking the pond. With friendly and attentive staff, On Cranberry Pond Bed & Breakfast is the perfect retreat for those looking to unwind and rejuvenate in a serene setting.

Welcome to AMC Ponkapoag Family Camp, your perfect getaway nestled in the heart of Randolph, Massachusetts. Located conveniently on Randolph Street, our camp serves as an idyllic escape for nature enthusiasts and families seeking a blend of adventure and relaxation. As a premier campground, lodging, and park destination, we offer a serene environment surrounded by lush greenery, pristine landscapes, and the tranquil Ponkapoag Pond. At AMC Ponkapoag Family Camp, we provide a variety of accommodations to suit your needs, from rustic cabins and cozy lodges to spacious campsites ideal for tents and RVs. Our facilities are designed to ensure a comfortable and enjoyable stay, featuring amenities such as picnic areas, fire pits, and clean restrooms.

Captain's Bounty On The Beach is a charming lodging establishment located at 1 Beach Street in the beautiful town of Rockport, Massachusetts, United States. Situated right on the beach, guests can enjoy stunning ocean views and the sound of waves crashing against the shore. The cozy rooms are decorated in a nautical theme, paying homage to the town's maritime history. Guests can relax on the private balcony or patio and take in the fresh sea air. The friendly staff are always on hand to ensure guests have a comfortable and enjoyable stay. Captain's Bounty On The Beach is the perfect seaside retreat for those looking to unwind and relax by the water.

Surfcomber On The Ocean is a charming lodging institution located at 107 South Shore Drive in Yarmouth, Massachusetts, United States. Situated right on the ocean, guests can enjoy stunning views of the water and easy access to the beach. The Surfcomber offers comfortable accommodations, friendly service, and a relaxing atmosphere perfect for a beach getaway. Whether you're looking to relax on the sand, explore the nearby attractions, or simply unwind by the ocean, Surfcomber On The Ocean is the ideal destination for your next vacation.

The Inn on the Beach is a charming lodging located at 16 Bank Street in Harwich, Massachusetts, United States. Situated right on the beach, this cozy inn offers guests a peaceful and relaxing retreat with stunning ocean views. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the morning and spend their days lounging on the sandy shores or exploring the nearby attractions. Whether you're looking for a romantic getaway or a family vacation, the Inn on the Beach is the perfect destination for a memorable stay by the sea.

Ocean Club On Smugglers Beach is a luxurious lodging destination located at 329 South Shore Drive in Yarmouth, Massachusetts, United States. Situated right on the beautiful Smugglers Beach, this institution offers stunning ocean views and easy access to the sandy shores. Guests can relax in spacious and well-appointed rooms, take a dip in the outdoor pool, or enjoy delicious meals at the on-site restaurant. With its prime location and top-notch amenities, Ocean Club On Smugglers Beach is the perfect choice for a beachfront getaway.

Veranda Cape Cod Family Resort is a charming lodging located in Yarmouth, Massachusetts. Situated at 1261 Massachusetts 28, this cozy resort offers a perfect retreat for families looking to enjoy a relaxing vacation on Cape Cod. With comfortable accommodations, a range of amenities, and a convenient location near the beach and other attractions, Veranda Cape Cod Family Resort is the ideal choice for a memorable getaway. Whether you're looking to relax by the pool, explore the local area, or simply unwind in a peaceful setting, this resort has everything you need for a wonderful stay.

Anchorage On the Cove is a charming lodging located at 450 State Highway in Eastham, Massachusetts, United States. Situated right on the waterfront, this institution offers stunning views of the cove and a peaceful atmosphere for guests to relax and unwind. The accommodations are cozy and comfortable, perfect for a weekend getaway or a longer stay on Cape Cod. With its convenient location near beaches, hiking trails, and local attractions, Anchorage On the Cove is the ideal spot for a memorable vacation in the heart of New England.

Dream Day on Cape Cod is a non-profit organization dedicated to providing respite and support for families with children facing serious illness. Located at 165 Nan Ke Rafe Path in Brewster, Massachusetts, this institution offers a unique and peaceful retreat for families to relax, connect with nature, and create lasting memories. With access to beautiful beaches, serene walking trails, and a variety of recreational activities, Dream Day on Cape Cod provides a much-needed break from the challenges of everyday life. Families can come together to enjoy quality time together and find comfort and healing in the beauty of Cape Cod.

Fourth Cliff Family Recreation Area is a charming campground, lodging, and park located at 348 Central Avenue in Scituate, Massachusetts, United States. Nestled in a picturesque setting, this institution offers a relaxing retreat for families and nature enthusiasts alike. With a variety of accommodations, including cabins and campsites, guests can enjoy a peaceful stay surrounded by the beauty of the outdoors. The park features amenities such as hiking trails, playgrounds, and picnic areas, providing endless opportunities for outdoor recreation and relaxation. Whether you're looking to unwind in nature or embark on an adventure, Fourth Cliff Family Recreation Area is the perfect destination for a memorable getaway.

Blue - Inn on the Beach is a charming lodging located at 20 Fordham Way in Newbury, Massachusetts, United States. Situated right on the beach, guests can enjoy stunning ocean views and easy access to the sand and surf. The inn offers comfortable accommodations with a cozy, beachy vibe, perfect for a relaxing getaway. With friendly staff and a convenient location, Blue - Inn on the Beach is the ideal spot for a seaside retreat.

Grand Slam Entertainment is a premier family fun destination located in Harwich, Massachusetts on Cape Cod. Visitors can enjoy a variety of exciting activities including bumper boats, batting cages, zip lining, and more. Whether you're looking for a thrilling adventure or a fun day out with the family, Grand Slam Entertainment has something for everyone. Come visit us at 322 Main Street and create unforgettable memories on Cape Cod!

Village Green Family Campground is a peaceful retreat nestled in the heart of Brimfield, Massachusetts. Situated at 228 Sturbridge Road, this charming campground offers a variety of accommodations for families looking to relax and reconnect with nature. With spacious RV sites, cozy cabins, and tent camping options, there is something for everyone at Village Green. Guests can enjoy the lush green surroundings, take a dip in the swimming pool, or explore the hiking trails that wind through the campground. The on-site store has all the essentials you need for a comfortable stay, from firewood to snacks and souvenirs.

Bluegreen Vacations The Soundings, Ascend Resort Collection is a charming lodging institution located at 79 Chase Avenue in Dennis, Massachusetts, United States. Situated right on the beautiful shores of Cape Cod, this resort offers guests a peaceful and picturesque getaway. The accommodations are spacious and comfortable, with modern amenities and stunning views of the ocean. Guests can relax by the outdoor pool, take a stroll along the beach, or explore the nearby attractions such as museums, shops, and restaurants. Whether you're looking for a romantic retreat or a fun family vacation, Bluegreen Vacations The Soundings is the perfect destination.

Pelham on Earle is a charming lodging institution situated at 30 Earle Road in the picturesque town of Harwich, Massachusetts. This cozy retreat offers a peaceful and serene atmosphere, perfect for a relaxing getaway. The rooms are tastefully decorated and equipped with all the necessary amenities to ensure a comfortable stay. Guests can enjoy the beautiful surroundings and explore the nearby beaches and attractions. Whether you are looking for a romantic escape or a family vacation, Pelham on Earle is the ideal choice for a memorable stay in Cape Cod.

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.

The Inn On Onset Bay is a charming lodging located at 181 Onset Avenue in Wareham, Massachusetts. Situated right on the picturesque Onset Bay, this cozy inn offers comfortable accommodations with beautiful views of the water. Guests can enjoy a relaxing stay in one of the well-appointed rooms and take advantage of the convenient location near local attractions, shops, and restaurants. Whether you're looking for a peaceful getaway or a fun-filled vacation, the Inn On Onset Bay is the perfect choice for your stay in Wareham.

Pelham on Main is a charming lodging establishment located at 829 Main Street in Dennis, Massachusetts. This cozy inn offers a warm and inviting atmosphere for guests looking to relax and unwind on their vacation. The rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Situated in the heart of town, Pelham on Main is within walking distance to local shops, restaurants, and attractions, making it the perfect home base for exploring all that Dennis has to offer. Whether you're visiting for a weekend getaway or an extended stay, Pelham on Main is the ideal choice for your accommodation needs.

The Island Inn on Martha's Vineyard by Vacasa is a charming vacation destination located at 30 Island Inn Road in Oak Bluffs, Massachusetts, United States. This condominium resort sits on five acres of beautiful land and is open year-round, offering a perfect New England getaway. The Island Inn on Martha's Vineyard offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for a cozy retreat for two or a spacious home for the whole family, there is something for everyone. The property boasts 51 vacation rentals with internet access, allowing guests to stay connected during their stay.

FearlessRose vacation rental is a cozy and welcoming lodging institution located on Appleton Street in Springfield, Massachusetts, United States. Our rental property offers a comfortable and stylish accommodation option for travelers looking to experience the charm of Springfield. With modern amenities, spacious rooms, and a convenient location, FearlessRose vacation rental is the perfect choice for a relaxing and enjoyable stay in the area. Whether you are visiting for business or pleasure, our institution provides a peaceful retreat where you can unwind and recharge during your trip. Book your stay with us today and experience the comfort and convenience of FearlessRose vacation rental.

My Cape Cod Vacation Home is a coastal retreat located in Dennis Port, Massachusetts, offering a peaceful getaway on beautiful Cape Cod. Our lodging establishment features 5 uniquely designed guest rooms, each providing a tranquil environment for a restful night's sleep. Situated within walking distance to the beach, guests can enjoy the sun, sand, and surf just moments away. Additionally, our property boasts a cozy fire pit for evening relaxation and central air conditioning for ultimate comfort. Whether you're looking for a relaxing beach vacation or a convenient home base for exploring all that Cape Cod has to offer, My Cape Cod Vacation Home is the perfect choice.

On the Cove is a charming lodging institution located at 20 Andrews Street in Gloucester, Massachusetts. Nestled on the picturesque coast of Cape Ann, this cozy retreat offers guests a peaceful and relaxing getaway. With stunning views of the cove and easy access to the beach, On the Cove is the perfect destination for those looking to unwind and rejuvenate. The accommodations are comfortable and inviting, and the friendly staff are always on hand to ensure a memorable stay. Whether you're seeking a romantic weekend escape or a family vacation by the sea, On the Cove is the ideal choice for your next trip to Gloucester.

The Calico Seahorse-Beach Vacation Rentals is a unique institution located at 90 White Horse Road in Plymouth, Massachusetts, United States. As a real estate and travel agency, we offer 7 beach-themed bungalows just a 5-minute walk from White Horse Beach. Each bungalow is a dream destination, fully furnished with everything you need for a beach getaway, including a beach wagon filled with chairs, umbrellas, and boogie boards, as well as an outdoor shower, community fire pit, and your own gas grill. Our accommodations include a Studio that sleeps 2, three 1-bedroom bungalows that sleep 5, two 2-bedroom bungalows that sleep 7, and a 4-bedroom Main house that sleeps 11. All of our bungalows are fully stocked with a kitchen, stainless steel appliances, drip coffee maker, and a Keurig. Each bungalow is themed after places we have traveled around the world, adding a colorful and whimsical touch to the property.