TOP 30 Best Private cottages in Massachusetts

The Captain Freeman Inn, located at 15 Breakwater Road in Brewster, Massachusetts, is a beautifully restored Sea Captain's mansion just a short walk away from Breakwater Beach. This award-winning Bed and Breakfast has been recognized with the Tripadvisor Certificate of Excellence for the past 11 years, offering guests a deluxe seaside experience year-round. Guests can enjoy the outdoor heated salt water swimming pool and custom firepit, providing the ultimate in luxury and relaxation in every season. The inn also offers a gourmet three-course breakfast made with farm-to-table ingredients, served in a charming indoor dining area or on the screened porch.

Plan Sea Adventure Charters, located at 53 Dock Street in Edgartown, Massachusetts, is the premier boat tour and rental company in Martha’s Vineyard and Cape Cod. Offering a variety of private cruise packages for groups of up to 18 passengers, our boat tours are perfect for family outings, bachelorette parties, team building events, and more. Our experienced Captains, with U.S. Coast Guard Masters Licenses, ensure a safe and enjoyable experience as you cruise along the beautiful shoreline of Woods Hole and Oak Bluffs. With indoor and outdoor heated seating, a bathroom, and a wet bar on board, our classic New England motor vessels provide a luxurious and comfortable ride for all guests.

Catboat Charters is a premier travel agency located at 1 Dock Street in Edgartown, Massachusetts. Specializing in unique and unforgettable sailing experiences, Catboat Charters offers a variety of charter options for exploring the beautiful waters of Martha's Vineyard and beyond. Whether you're looking for a relaxing sunset cruise or an adventurous day of sailing, Catboat Charters has something for everyone. With experienced captains and top-notch service, Catboat Charters is the perfect choice for your next nautical adventure.

New England Maids, located at 18R Rochester Road in Carver, Massachusetts, is more than just a typical laundry service. We understand the importance of trust when letting someone into your home, which is why we offer peace of mind along with our cleaning services. Our team is dedicated to ensuring that you feel safe and comfortable with us in your space. When you choose New England Maids for your cleaning needs in the South Shore, you become part of a family that values safety, respect, and professionalism. Our cleaning services go beyond the basics to provide a thorough and trustworthy experience.

Welcome to The Needle Group-Sharon, MA Realtors-REAL Broker, your premier real estate agency located at 62 South Main Street, Sharon, Massachusetts. We are dedicated to providing exceptional real estate services to our clients, offering a comprehensive platform for searching homes, condos, land, and foreclosure properties. Our website is your ultimate resource, updated every 15 minutes by the official Realtor® database, ensuring you have access to the most current listings. With easy-to-use features, you can save searches, receive daily email alerts on new listings, and stay informed with market reports. Led by Dianne S. Needle, an award-winning Realtor with over 25 years of experience, our team is committed to helping you achieve your real estate goals. Dianne is renowned for her expert market knowledge and personalized approach, ensuring every client receives remarkable service. Under her leadership, The Needle Group has earned accolades such as being ranked number two in the “TOP 25 SMALL TEAMS-USA” and receiving the prestigious Elite Agent award with REAL Broker annually.

Kiklis Real Estate - Your Trusted Partner in Real Estate Welcome to Kiklis Real Estate, your premier real estate agency located at 42 Pleasant Street, Woburn, Massachusetts. With a deep commitment to personalized service and a wealth of experience in the Woburn area, our team of expert agents is dedicated to helping you achieve your real estate goals, whether you're buying or selling a home.

Welcome to Jennifer Keenan | Realtor | 4Squares Residential Group @ Keller Williams Realty, your trusted partner in real estate located at 250 Grove Street, Medford, Massachusetts. As a Massachusetts native and seasoned Realtor®, Jennifer Keenan brings a deep passion for New England living and an intimate knowledge of the hidden gems that each town has to offer. With nearly two decades of experience in the private sector as an Advertising Account Manager for some of Greater Boston's top employers, Jennifer has honed her skills in customer service, ensuring that every client receives personalized and attentive care. Jennifer's dedication to her clients goes beyond transactions, as many have become close friends over the years. Whether you are buying, selling, or investing in real estate, Jennifer is committed to guiding you through every step of the process with expertise and integrity.

Brian Gagnon Luxury Real Estate Agent Welcome to Brian Gagnon Luxury Real Estate, your premier destination for Boston condos and real estate. Located conveniently at 399 Boylston Street, Boston, Massachusetts, our agency stands as a beacon of excellence and personal touch in the bustling real estate market of Boston.

Welcome to Broad Sound Real Estate, your premier destination for all your real estate needs in Revere, Massachusetts, and the Greater Boston Area. Conveniently located at 375 Broadway, Revere, MA 02151, we are dedicated to providing exceptional real estate services, whether you are buying, selling, renting, or investing. Discover the luxury of Surfside Lofts, where breathtaking ocean views meet contemporary design in a spacious loft-style penthouse. With over 1,400 square feet of modern elegance, complemented by floor-to-ceiling windows and a private 500 square foot roof deck, this property is perfect for entertaining and enjoying the stunning coastal scenery. Take advantage of the vibrant Revere culinary scene just a stroll away at Waterfront Square.

Welcome to Chubb Homes Team Boston, your premier real estate agency located at 1266 Furnace Brook Parkway, Quincy, Massachusetts. We specialize in providing exceptional real estate services in the Boston area and are here to help you navigate this dynamic market with ease and confidence. At Chubb Homes Team Boston, we pride ourselves on being the first to alert you when new listings that match your criteria hit the market. Our comprehensive property search tool on Boston2.com allows you to explore ALL homes for sale from ALL real estate brokers in Boston and the surrounding areas. Whether you're interested in the vibrant neighborhoods of South Boston or the historic charm of Beacon Hill, our interactive map search makes it easy to find the newest homes on the market.

The Guest House at Field Farm is a charming lodging establishment located at 554 Sloan Road in beautiful Williamstown, Massachusetts. Nestled in the picturesque countryside, this guest house offers a peaceful and serene retreat for visitors looking to escape the hustle and bustle of city life. With comfortable accommodations, stunning views of the surrounding landscape, and warm hospitality, The Guest House at Field Farm is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution provides a welcoming and cozy atmosphere for all guests.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

The Dancing Bear Guest House, also known as Blooming Inn, is a charming accommodation option located in the heart of Shelburne Falls, Massachusetts. Housed in the historic Moses W. Merrill homestead dating back to 1852, this inn offers comfortable lodgings in a setting that exudes historic elegance. Each room is equipped with a private bathroom for convenience, and guests can enjoy spacious living and dining rooms for relaxation. The inn also provides self-serve coffee, tea, and toast-making facilities, as well as access to a refrigerator for storing personal food items. Guests can customize their breakfast with English Muffins and special bread, adding to the flexibility of their morning routine. Additionally, the lovely garden and outdoor breakfast option enhance the overall guest experience, providing a serene setting for a memorable stay. The cozy guest sitting rooms and dining room offer inviting spaces for socializing, reading, or enjoying a quiet moment. With amenities like fireplaces and scenic views, these common areas enhance comfort and relaxation. Whether visiting for a short-term stay or longer duration, the Dancing Bear Guest House AKA Blooming Inn offers a convenient and pleasant lodging option within a historic setting.

Maguire House Bed & Breakfast is a charming and cozy lodging establishment located at 30 Cobb Road in Ashburnham, Massachusetts, United States. Nestled in a picturesque setting, this bed and breakfast offers a warm and welcoming atmosphere for guests looking for a peaceful retreat. The historic house features comfortable rooms with modern amenities, delicious homemade breakfast served each morning, and friendly hospitality from the owners. Whether you are visiting for a romantic getaway, a family vacation, or a business trip, Maguire House Bed & Breakfast is the perfect place to relax and unwind in a beautiful New England setting.

Kaede Bed & Breakfast is a charming lodging located at 16 North Main Street in historic Ipswich, Massachusetts. Since 2006, we have welcomed visitors to our Federalist building, also known as the Colburn Home, offering a unique blend of Japanese culture and New England charm. Guests can enjoy a delicious cooked-to-order breakfast each morning, with both Western and Japanese options available. As an owner-operated establishment, we prioritize communication, accountability, and flexibility to ensure a personalized experience for every guest.

Delano Homestead Bed & Breakfast is a charming and historic lodging establishment located at 39 Walnut Street in Fairhaven, Massachusetts. This beautifully restored bed and breakfast offers guests a cozy and welcoming atmosphere, with comfortable rooms and modern amenities. The inn is situated in a convenient location, close to local attractions such as Fort Phoenix State Reservation and the New Bedford Whaling Museum. Whether you are visiting for a romantic getaway or a relaxing vacation, Delano Homestead Bed & Breakfast is the perfect place to stay. Experience warm hospitality and a true taste of New England charm at this lovely inn.

The Onset Beach Compound is a luxurious Cape Cod beach resort and oceanic habitat located at 35 East Boulevard in Wareham, Massachusetts, United States. This idyllic retreat offers a perfect blend of relaxation and adventure, with stunning views of the ocean and access to pristine sandy beaches. Guests can enjoy a range of amenities including spacious accommodations, fine dining options, and recreational activities such as swimming, kayaking, and beachcombing. Whether you're seeking a romantic getaway or a fun-filled family vacation, The Onset Beach Compound is the perfect destination for your next seaside escape.

Welcome to Brimblecomb Hill Bed & Breakfast, located in the charming town of Marblehead, Massachusetts. Our historic inn offers a cozy and inviting atmosphere for guests looking for a relaxing getaway. Situated at 33 Mechanic Street, our convenient location allows easy access to the town's shops, restaurants, and attractions. Our lodging features comfortable rooms with modern amenities, delicious breakfast options, and friendly staff ready to assist you during your stay. Whether you are visiting for a weekend getaway or a longer vacation, Brimblecomb Hill Bed & Breakfast is the perfect place to unwind and experience the beauty of Marblehead.

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.

CAPTAIN MORSE HOUSE Vacation Rental is a charming lodging option located at 80 North Water Street in the picturesque town of Edgartown, Massachusetts. This historic property offers a unique and cozy atmosphere for guests looking to experience the beauty of Martha's Vineyard. As a real estate and travel agency, CAPTAIN MORSE HOUSE Vacation Rental provides top-notch customer service and a range of accommodation options to suit every traveler's needs. Whether you're looking for a romantic getaway or a family vacation, this institution is the perfect choice for your next holiday.

Flip and Hold Funding & Realty is a reputable real estate agency located at 681 Broadway in Raynham, Massachusetts. We specialize in helping clients with their real estate investments, whether they are looking to flip properties for a profit or hold onto them for long-term growth. Our experienced team of professionals is dedicated to providing top-notch service and guidance to ensure our clients make sound investment decisions. Contact us today to learn more about how we can help you achieve your real estate goals.

Welcome to MANSARD Commercial Properties, your trusted partner in commercial real estate located at 14 Essex Street, Andover, Massachusetts. As Greater Boston’s premier commercial real estate broker, we specialize in connecting property owners with the right buyers to ensure a smooth, profitable transaction. With over 19 years of experience and more than 1,000 successful property sales, MANSARD is recognized as one of the most successful commercial real estate brokerages in Massachusetts, as noted by the Boston Business Journal. Our team, led by Jeremy Cyrier, CCIM, is committed to providing personalized service and expert advice, ensuring 88.9% of our deals close on time at the seller's accepted offer price.

Welcome to Mango Realty Inc., your trusted real estate agency located at 38 Main Street, Saugus, Massachusetts. We specialize in connecting you with the best residential and investment properties in the area. Whether you're a first-time homebuyer, an experienced investor, or looking to sell your property, our dedicated team is here to guide you through every step of the real estate process. Our listings feature a diverse range of properties, including well-maintained multi-family homes, stunning single-family residences, and charming coastal homes. We pride ourselves on offering properties in sought-after locations like Old Nugent Farm and West Peabody, known for their serene environments and excellent community amenities.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

Five Bridge Inn is a charming lodging establishment situated at 152 Pine Street in Rehoboth, Massachusetts. This picturesque inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by lush greenery and five scenic bridges, the inn provides a tranquil atmosphere for a memorable stay. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable experience. Guests can enjoy a delicious breakfast in the morning and unwind in the beautiful outdoor spaces. Whether you are looking for a romantic getaway or a peaceful weekend retreat, Five Bridge Inn is the perfect destination for a memorable stay in Massachusetts.

Located in the charming town of Newburyport, Massachusetts, the Compass Rose Inn offers a cozy and welcoming lodging experience. Situated at 5 1/2 Center Street, this quaint inn is the perfect destination for travelers seeking a peaceful retreat. The Compass Rose Inn boasts comfortable accommodations, friendly staff, and a convenient location near local attractions and dining options. Whether you're visiting for business or pleasure, you'll feel right at home at the Compass Rose Inn.

Welcome to The Merchant, a charming lodging establishment located at 148 Washington Street in the historic city of Salem, Massachusetts. Our boutique hotel offers a unique and cozy atmosphere, perfect for travelers looking for a comfortable and memorable stay. The Merchant is conveniently situated in the heart of Salem, just steps away from local attractions, shops, and restaurants. Our friendly staff is dedicated to providing exceptional service to ensure your stay is enjoyable and stress-free. Whether you are visiting for business or pleasure, The Merchant is the perfect choice for your accommodation needs in Salem.

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.

The Cove At Rockport is a charming lodging located at 1 King Street in the picturesque town of Rockport, Massachusetts. Situated in the United States, this institution offers cozy accommodations with stunning views of the surrounding area. Guests can enjoy a peaceful retreat by the sea, with easy access to local attractions, shops, and restaurants. Whether you're looking for a romantic getaway or a family vacation, The Cove At Rockport provides a comfortable and welcoming atmosphere for all travelers.