TOP 30 Best Winter vacation in Massachusetts

Jiminy Peak Vacation Home Rentals is a real estate and travel agency located at 37 Corey Road in Hancock, Massachusetts, United States. We offer cozy vacation homes perfect for winter weekends, holiday periods, and spring, summer, and fall getaways. For winter weekends and holiday periods, we require a 7-day cancellation notice with a 10% cancellation fee of the total reservation. For midweek stays during non-holiday periods, we require a 48-hour cancellation notice with the same cancellation fee policy.

Atlantic Vacation Homes is a premier vacation rental and real estate company located in Cape Ann, Massachusetts. With 40 years of experience, we specialize in creating dream vacations for our guests in Gloucester, Rockport, and throughout Boston's North Shore. Our properties are situated in sea-faring communities known for some of the best beaches on the east coast. From pristine beaches to world-class museums, art colonies, festivals, and fresh seafood, Cape Ann has something for everyone. Our vacation rentals cater to every need and budget, offering a comfortable and convenient stay with stunning views and central locations. We prioritize diversity and inclusion, creating a welcoming and respectful environment for our guests, employees, and community partners. As a locally owned company, we give back to the community through supporting local organizations and initiatives. Book your stay with Atlantic Vacation Homes for a memorable and enjoyable experience on Boston's North Shore.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located at 374 Commercial Street in picturesque Provincetown, Massachusetts. With a wide range of vacation rental properties to choose from, Kinlin Grover offers luxury accommodations for every traveler's needs. Whether you're looking for a cozy beachfront cottage or a spacious waterfront estate, their team of experienced agents is dedicated to helping you find the perfect vacation rental. With a reputation for exceptional customer service and attention to detail, Kinlin Grover Vacation Rentals is the go-to agency for your next getaway in Provincetown.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located at 1990 Main Street in Brewster, Massachusetts. Specializing in vacation rentals, they offer a wide range of properties for visitors looking to experience the beauty of Cape Cod. Whether you're looking for a beachfront cottage, a cozy cabin in the woods, or a luxurious oceanfront estate, Kinlin Grover has the perfect accommodation for your getaway. With exceptional customer service and a dedication to providing top-notch accommodations, Kinlin Grover Vacation Rentals is the go-to agency for your next Cape Cod vacation.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located at 1094 Main Street in Yarmouth, Massachusetts. Specializing in vacation rentals, Kinlin Grover offers a wide range of luxurious properties for visitors looking to experience the beauty of Cape Cod. With a team of dedicated professionals, Kinlin Grover provides top-notch customer service and expert guidance to help clients find the perfect vacation rental for their needs. Whether you're looking for a beachfront cottage or a spacious family home, Kinlin Grover has a diverse portfolio of properties to choose from. Trust Kinlin Grover Vacation Rentals to make your Cape Cod vacation truly unforgettable.

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!

Del Mar Vacations - Chatham Rentals is a reputable real estate and travel agency located at 30 Captain Richards Way in Chatham, Massachusetts. Specializing in vacation rentals in the charming town of Chatham, this institution offers a wide range of properties for visitors looking to explore Cape Cod. Whether you're searching for a cozy beachfront cottage or a luxurious waterfront estate, Del Mar Vacations - Chatham Rentals has the perfect accommodation for your getaway. With exceptional customer service and a commitment to providing top-notch accommodations, this agency ensures that your vacation experience is nothing short of unforgettable. Book your next Cape Cod vacation with Del Mar Vacations - Chatham Rentals and create lasting memories in this beautiful coastal destination.

Bonnie's Travel - Your Vacation Station is a premier travel agency located at 36 Hope Street in Seekonk, Massachusetts. Our dedicated team of travel experts is committed to helping you plan the perfect getaway, whether it's a relaxing beach vacation, an adventurous safari, or a romantic European tour. With personalized service and attention to detail, we strive to make your travel dreams a reality. Stop by our office or give us a call to start planning your next unforgettable vacation experience with Bonnie's Travel - Your Vacation Station.

Cape Cod Beach Vacations is a premier real estate and travel agency located at 598 Washington Street in Canton, Massachusetts, United States. Specializing in luxury beachfront properties and vacation rentals on the picturesque Cape Cod peninsula, our experienced team is dedicated to helping you find the perfect seaside escape. Whether you're looking for a cozy cottage for a romantic getaway or a spacious beach house for a family vacation, Cape Cod Beach Vacations has the ideal accommodation for your needs. Book your dream beach vacation with us today and create unforgettable memories by the ocean.

Winter Rendezvous is a premier travel agency located at 50 Victory Road in Boston, Massachusetts. Specializing in winter getaways, our expert team is dedicated to creating unforgettable experiences for our clients. Whether you're looking for a cozy ski resort, a thrilling snowboarding adventure, or a relaxing winter retreat, Winter Rendezvous has you covered. Let us help you plan the perfect winter escape and make memories that will last a lifetime.

Sandpiper Rentals is a premier real estate and travel agency located in the charming town of Edgartown, Massachusetts. Specializing in Martha's Vineyard vacation rentals, we offer a wide range of luxurious properties to choose from for your next getaway. Whether you are looking for a cozy cottage by the beach or a spacious waterfront estate, our team of experts is dedicated to helping you find the perfect vacation rental to suit your needs. With our convenient location on Winter Street, we are just a short distance away from all the attractions and activities that Martha's Vineyard has to offer. Trust Sandpiper Rentals to make your vacation dreams a reality.

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.

Winter Island/Waikiki Beach is a picturesque park and tourist attraction located at 60 Winter Island Road in Salem, Massachusetts, United States. This stunning destination offers visitors a beautiful sandy beach overlooking the Atlantic Ocean, perfect for swimming, sunbathing, and picnicking. With its serene atmosphere and breathtaking views, Winter Island/Waikiki Beach is the ideal spot for a relaxing day by the water. Explore the surrounding nature trails, enjoy a leisurely stroll along the shoreline, or simply unwind and take in the peaceful surroundings. Whether you're looking for a fun day out with family and friends or a tranquil retreat from the hustle and bustle of everyday life, Winter Island/Waikiki Beach is sure to leave you feeling refreshed and rejuvenated.

The Sydney is a charming lodging establishment located at 22 Winter Street in the picturesque town of Edgartown, Massachusetts, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind during their stay on Martha's Vineyard. With its convenient location near shops, restaurants, and attractions, The Sydney is the perfect home base for exploring all that this beautiful island has to offer. Whether you're seeking a romantic getaway or a family vacation, The Sydney has everything you need for a memorable and enjoyable experience.

Point B Realty is a premier real estate and travel agency located in the charming town of Edgartown, Massachusetts. Situated at 19 Winter Street, our dedicated team of professionals are committed to helping clients find their dream vacation rental or forever home on the beautiful island of Martha's Vineyard. Whether you're looking for a cozy beachfront cottage or a luxurious estate, Point B Realty has the expertise and local knowledge to make your real estate dreams a reality. Additionally, our travel agency services can assist with planning the perfect Martha's Vineyard getaway, from accommodations to activities. Trust Point B Realty to provide unparalleled service and expertise in all your real estate and travel needs.

Sandpiper Realty, Inc. is a premier real estate agency located at 60 Winter Street in Edgartown, Massachusetts, United States. Specializing in Martha's Vineyard real estate, we have been serving clients for over 50 years. Martha's Vineyard, a historic and picturesque island just off the Massachusetts coast, offers stunning beaches, waterfront properties, and New England architecture. Our team of experienced Martha's Vineyard Realtors® can help you find the perfect vacation home or assist in buying or selling property on the Island. Whether you are looking for a relaxing getaway or a new permanent residence, we are here to make your real estate experience seamless and enjoyable. Visit us at Sandpiper Rentals, Inc. to explore Martha's Vineyard vacation rentals and start your journey to owning a piece of this magical seaside destination.

Martha's Vineyard Real Estate, located at 63 Winter Street in Edgartown, Massachusetts, is a reputable real estate agency with a rich history dating back to 1972. Originally a peaceful retreat for families to escape to, Martha's Vineyard has since evolved into a bustling community with diverse real estate transactions. Despite the changes over the years, Martha's Vineyard Real Estate still prides itself on building personal connections with clients that last long after the transaction is complete. The agency's agents have a strong working knowledge of the island's real estate market and are committed to providing individual attention to each client.

Ambergris Gables & Owl's Nest Cottage is a charming and historical vacation rental located in Eastham, Massachusetts. Situated on a private one acre lot, this well-appointed property is perfect for families looking to escape and explore the beauty of Cape Cod. With three bedrooms in the main house and an additional cottage, there is plenty of space for up to eight guests. The property features three full bathrooms, a steam shower, outdoor shower covered in roses, and a fully equipped kitchen perfect for family meals. The Owl's Nest Cottage, constructed with reclaimed wood, offers a cozy retreat with a wrap-around porch and wood-burning fireplace. Guests can enjoy nearby beaches, hiking trails, and local attractions, making it an ideal location for a relaxing getaway. The hosts, Nick and Trina, are attentive and responsive, ensuring a memorable stay for all guests. Whether you're looking to relax on the beach or explore the Cape, Ambergris Gables & Owl's Nest Cottage is the perfect vacation rental for your next trip to Eastham.

Tavera's Shipping & Travel is a reputable travel agency located at 138 Winter Street in Haverhill, Massachusetts, United States. Our dedicated team of professionals is committed to providing exceptional service and expertise for all your travel needs. Whether you are looking to book a dream vacation, plan a business trip, or ship belongings internationally, Tavera's Shipping & Travel is here to assist you every step of the way. Contact us today to start planning your next adventure!

Country Ski & Sport Inc. is a premier ski and snowboard store located at 901 Winter Street in Hanson, Massachusetts. Established in 1970, our flagship store has been serving the Boston area for over 50 years, providing top-quality winter sports equipment, apparel, and accessories. While our physical stores are currently closed for the season, we invite you to shop online at any time. Our stores will re-open in August for the upcoming winter season. We offer a range of services including in-store shopping, personal appointments, online ordering, leasing options, and more. Visit us for all your winter sports needs!

Wendy Harman, Point B Realty, LLC is a premier real estate agency located at 19 Winter Street in Edgartown, Massachusetts. With a strong reputation for exceptional service and expertise in the local real estate market, Wendy Harman and her team at Point B Realty are dedicated to helping clients find their dream homes on Martha's Vineyard. Whether you are looking to buy, sell, or rent a property, Wendy Harman, Point B Realty, LLC is committed to providing personalized and professional assistance every step of the way. Contact them today to start your real estate journey in Edgartown, Massachusetts.

Sail Salem is a non-profit organization located at 50 Winter Island Road in Salem, Massachusetts. Our mission is to provide affordable and accessible sailing opportunities for people of all ages and abilities. Whether you are a beginner looking to learn the basics or an experienced sailor wanting to hone your skills, Sail Salem has something for everyone. Our experienced instructors offer a variety of classes and programs, including youth sailing camps, adult lessons, and group outings. Come join us on the water and experience the joy of sailing in the historic city of Salem.

Welcome to Elite Luxury Rentals – Elevate Your Dreams to Reality Located at 295 Winter Street, Hanover, Massachusetts, Elite Luxury Rentals is your premier destination for experiencing unparalleled luxury and style. Serving the Boston area, Cape Cod, and the entirety of Massachusetts, we specialize in offering a curated collection of the finest automobiles, luxury charters, and exquisite vacation rentals.

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.

Butternut Ski Area and Tubing Center is a popular tourist attraction located at 380 State Road in Great Barrington, Massachusetts. This institution offers a wide range of winter activities for visitors to enjoy, including skiing, snowboarding, and tubing. The ski area features well-maintained slopes for all skill levels, while the tubing center provides a thrilling experience for all ages. With stunning views of the surrounding area and top-notch facilities, Butternut Ski Area and Tubing Center is the perfect destination for outdoor enthusiasts looking for a fun and exciting winter adventure.

Howe State Park is a picturesque park located at 48 Howe Road in Spencer, Massachusetts, United States. This popular tourist attraction offers visitors a peaceful escape into nature with its lush greenery, scenic walking trails, and tranquil picnic areas. Whether you're looking to relax with a leisurely stroll or enjoy a family outing, Howe State Park is the perfect destination for outdoor enthusiasts of all ages. With its convenient location and serene atmosphere, this park is a must-visit for anyone looking to experience the beauty of nature in Massachusetts.

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.

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.

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.

Welcome to Inn on the Sound at Falmouth, a charming oceanfront bed and breakfast located in the popular beach community of Falmouth on Cape Cod, Massachusetts. Situated high on a bluff, our inn offers breathtaking views of the ocean, perfect for watching the sunrise, sunset, and even the moon rise over the sound between the upper Cape and Martha's Vineyard. Guests can enjoy our comfortable and relaxed guest rooms, all with private baths and some with private balconies. Our beautifully decorated living room provides a front-row seat for the Fourth of July fireworks, while our dining room and deck offer delicious homemade breakfasts to start your day off right.