TOP 30 Best Private cottages in Massachusetts

Cottage Street Advisors is an SEC registered fee-only investment advisory firm located at 9 Cottage Street in Marion, Massachusetts. We specialize in meeting the specific needs of high net worth clients and families, managing over one hundred discreet portfolios for approximately fifty clients. Our services include individualized portfolio management and financial strategy and planning advice, with a focus on long-term, patient, value investing. Our founder and Managing Partner, Michael K. Davis, brings thirty-five years of professional investment management experience to the firm. He is joined by Senior Partner Jason Haviland, a CFA Charterholder with over twenty-five years of financial services and investment management experience. Helen Correale, our Office Manager, is an indispensable member of our team with nearly 15 years of experience at Cottage Street Advisors.

Cranberry Cottages is a charming accommodation located at 785 State Highway in Eastham, Massachusetts, United States. Nestled in a picturesque setting, Cranberry Cottages offers cozy and comfortable cottages for guests looking for a relaxing getaway on Cape Cod. Each cottage is tastefully decorated and fully equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the tranquil surroundings, explore the nearby beaches, or take a short drive to the bustling town center for shopping and dining. Whether you're looking for a romantic retreat or a family vacation, Cranberry Cottages provides the perfect setting for a memorable stay on the Cape.

The Cottages at Nantucket Boat Basin is a charming lodging option located at 24 Old South Wharf in Nantucket, Massachusetts. This unique institution offers cozy cottages with stunning views of the marina, perfect for a relaxing getaway. As a real estate agency, they also offer opportunities to invest in waterfront properties in this picturesque location. Additionally, as a travel agency, they can help plan your dream vacation to Nantucket, ensuring a memorable experience. Whether you're looking for a weekend retreat or a long-term investment, The Cottages at Nantucket Boat Basin has everything you need for a perfect stay in this beautiful coastal town.

Even'tide Resort & Cottages is a charming lodging establishment located in Wellfleet, Massachusetts. Situated at 650 U.S. 6, this resort offers cozy cottages and comfortable rooms for guests to enjoy a relaxing stay on Cape Cod. The resort is surrounded by beautiful scenery and is just a short drive away from the beach, making it the perfect destination for a seaside getaway. With friendly staff, clean accommodations, and a peaceful atmosphere, Even'tide Resort & Cottages is a great choice for those looking to unwind and rejuvenate in a tranquil setting.

Located at 135 South Shore Drive in Yarmouth, Massachusetts, Seaside Cottages offers a relaxing getaway on the oceanfront with a private beach overlooking Nantucket Sound. Our five-acre cottage colony is the perfect destination for couples and families looking to unwind and enjoy the beauty of Cape Cod. When you book directly with us, you won't have to worry about any additional booking or cleaning fees. Take advantage of our May special - stay 2 nights and get the 3rd night free! Or plan your fall getaway with our fall special - stay 2 nights and get the 3rd night 50% off. Just make sure to book online and note that blackout dates apply.

Truro Beach Cottages, located at 640 Shore Road in Truro, Massachusetts, offers a perfect escape for those looking to relax and unwind by the beach. Guests have raved about the cleanliness of the cottages, especially during these Covid times, and many have returned for another stay. The property is pet-friendly, making it a great option for those looking to bring their furry friends along for a vacation. The cottages provide a comfortable and stylish stay, with new flooring, kitchens, bathrooms, and mini-split AC systems. Guests can relax on the deck chairs and enjoy the stunning views of the dunes and the Atlantic Ocean. A short drive to downtown Truro and Provincetown offers a variety of activities, including art galleries, watersports, dining, and shopping.

equipped for cooking meals and the sound of the waves lulls you to sleep at night. Highly recommend for a peaceful and relaxing getaway.

Surf Side Cottages is a charming lodging option located at 370 Wilson Avenue in Wellfleet, Massachusetts, United States. This institution offers cozy and comfortable cottages for guests looking to enjoy a relaxing beach vacation. As a real estate agency, Surf Side Cottages also provides opportunities for those interested in purchasing a vacation home in this picturesque coastal town. Additionally, as a travel agency, they can assist guests in planning their ideal getaway to Wellfleet, whether it be for a weekend retreat or an extended stay. Experience the beauty of Cape Cod at Surf Side Cottages.

The Cottage Bar & Restaurant is a charming establishment located at 26 Union Street in the heart of Weymouth, Massachusetts. This cozy spot offers a warm and inviting atmosphere for guests to enjoy delicious food and drinks. Whether you're looking for a casual night out with friends or a special dinner with a loved one, The Cottage Bar & Restaurant is the perfect choice. With a diverse menu featuring a variety of tasty dishes and a well-stocked bar serving up refreshing cocktails, beers, and wines, there's something for everyone to enjoy. Come visit us at The Cottage Bar & Restaurant for a memorable dining experience in Weymouth.

Cottage Grove At Eastham is a charming lodging institution located at 1975 State Highway in Eastham, Massachusetts, United States. Nestled in a serene and picturesque setting, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests to relax and unwind. With its convenient location near popular attractions such as the Cape Cod National Seashore and Nauset Light Beach, Cottage Grove At Eastham provides the perfect base for exploring the beauty of Cape Cod. Whether you're looking for a romantic getaway or a family vacation, this charming establishment is sure to provide a memorable and enjoyable stay.

The Cottage at Blue Heron Farm is a charming lodging option located at 212 Warner Hill Road in the picturesque town of Charlemont, Massachusetts, United States. Situated on a serene farm property, guests can enjoy a peaceful retreat surrounded by nature. The cozy cottage offers comfortable accommodations and a tranquil atmosphere, perfect for a relaxing getaway. Whether you're looking to unwind in the countryside or explore the nearby attractions, The Cottage at Blue Heron Farm provides a unique and inviting place to stay.

Lighthouse Lane Cottages is a charming lodging option located at 5 Lighthouse Lane in Rockport, Massachusetts, United States. This institution offers cozy and well-appointed cottages for rent, making it the perfect accommodation choice for travelers looking for a peaceful and relaxing getaway. As a real estate agency, Lighthouse Lane Cottages also helps clients find their dream vacation home or investment property in the scenic coastal town of Rockport. Additionally, as a travel agency, they can assist guests in planning their itinerary and exploring the best attractions and activities in the area. Whether you are looking for a weekend escape or a long-term rental, Lighthouse Lane Cottages is your go-to destination for a memorable and enjoyable stay in Rockport.

The Ebb Tide Cottages is a charming lodging option located at 88 Chase Avenue in Dennis, Massachusetts, United States. Nestled near the picturesque coastline, this institution offers cozy and comfortable cottages for guests to enjoy a relaxing getaway by the sea. With its serene atmosphere and convenient location, The Ebb Tide Cottages is the perfect destination for those seeking a peaceful retreat on Cape Cod.

Fort Hill Bed and Breakfast offers a charming ocean-view cottage located at 75 Fort Hill Road in Eastham, Massachusetts. This cozy lodging option provides guests with a peaceful and picturesque retreat, perfect for those looking to relax and unwind by the sea. The cottage is well-appointed with comfortable furnishings and modern amenities, ensuring a comfortable stay for all visitors. Guests can enjoy stunning views of the ocean from the property, as well as easy access to nearby attractions such as the Cape Cod National Seashore and local restaurants and shops. Whether you're seeking a romantic getaway or a quiet escape, Fort Hill Bed and Breakfast's ocean-view cottage is the perfect choice for your next vacation.

Wheel In Cottages is a charming lodging establishment located in Eastham, Massachusetts, United States. As a real estate agency and travel agency, we offer cozy and comfortable cottages for your vacation getaway. Our cottages are equipped with all the amenities you need for a relaxing stay, including fully equipped kitchens, private bathrooms, and outdoor seating areas. Whether you're looking for a romantic retreat or a family vacation, Wheel In Cottages has the perfect accommodation for you. Book your stay with us today and experience the beauty of Cape Cod in style and comfort.

Gull Cottage Bed & Breakfast is a charming lodging establishment located at 50 Steele Road in Wellfleet, Massachusetts. Nestled in a picturesque coastal town, this cozy B&B offers a relaxing getaway for visitors looking to unwind and enjoy the beauty of Cape Cod. With comfortable accommodations, delicious homemade breakfasts, and personalized hospitality, Gull Cottage is the perfect home away from home for travelers seeking a peaceful retreat by the sea. Experience the warmth and charm of this quaint bed and breakfast during your next visit to Wellfleet.

Wellfleet Bayside Cottage is a charming lodging located at 65 Pier Road in the picturesque town of Wellfleet, Massachusetts. Nestled along the beautiful shores of the bay, this cozy cottage offers a peaceful retreat for guests looking to relax and unwind. The cottage features comfortable accommodations, a fully equipped kitchen, and a private deck with stunning views of the water. Whether you're looking for a romantic getaway or a family vacation, Wellfleet Bayside Cottage is the perfect destination for a memorable stay on the Cape.

The Clay Cottage is a charming pottery studio located at 2399 Swamp Road in Richmond, Massachusetts, United States. Our cozy studio offers a creative and relaxing environment for both beginners and experienced potters to explore their artistic talents. Our experienced instructors provide hands-on guidance and inspiration, ensuring that every student can create beautiful and unique pottery pieces. Whether you're looking to learn a new skill, unwind after a long day, or simply enjoy a fun outing with friends, The Clay Cottage is the perfect place to let your creativity flow. Join us for a pottery class, workshop, or private event and discover the joy of working with clay in our welcoming and supportive community.

Otwell Cottage is a charming lodging institution located at 24 North Beach Avenue in Bourne, Massachusetts, United States. This cozy cottage offers a relaxing and comfortable retreat for guests looking to enjoy a peaceful vacation by the beach. With its quaint decor, welcoming atmosphere, and convenient location, Otwell Cottage is the perfect choice for those seeking a memorable stay on Cape Cod. Immerse yourself in the beauty of the surroundings, unwind on the porch, and create lasting memories at this idyllic retreat in Bourne.

Topside Cottages is a charming accommodation located at 3 Knowles Heights Road in the picturesque town of Provincetown, Massachusetts. Nestled in a quiet residential neighborhood, these cozy cottages offer a peaceful retreat just minutes away from the bustling town center and beautiful beaches. Each cottage is uniquely decorated and equipped with modern amenities to ensure a comfortable stay for guests. With its convenient location and warm hospitality, Topside Cottages is the perfect choice for a memorable getaway on Cape Cod.

Located at 60 Ocean Drive in Dennis, Massachusetts, Uppvall Cottages is a real estate and travel agency that offers the perfect homeport for your Cape Cod vacation. Whether you're looking to relax on the beach, go windsurfing, or explore the many points of interest on the Cape, we have something for everyone. With 115 sandy beaches to choose from, including the Cape Cod National Seashore, there's no shortage of fun in the sun. Choose to vacation with us in the bustling months of July and August, or opt for a more peaceful experience at the beginning or end of the summer season. Create wonderful vacation memories with us at Uppvall Cottages.

The Cottage on Great Pond in Wellfleet, Massachusetts offers a tranquil and picturesque retreat for those looking to escape the hustle and bustle of everyday life. Located at 111 Wiles Lane, this charming lodging option provides guests with a cozy and comfortable stay surrounded by the natural beauty of the area. Whether you're looking to relax by the pond, explore the nearby beaches, or simply unwind in a peaceful setting, the Cottage on Great Pond is the perfect destination for a rejuvenating getaway. With its convenient location and welcoming atmosphere, this institution is sure to provide a memorable and enjoyable experience for all who stay here.

Gibson Cottages is a charming lodging institution located on Depot Road in the picturesque town of Eastham, Massachusetts, United States. Nestled in a peaceful and serene setting, Gibson Cottages offers cozy and comfortable accommodations for visitors looking to experience the beauty of Cape Cod. Each cottage is equipped with all the amenities needed for a relaxing stay, including kitchen facilities, spacious living areas, and private outdoor spaces. Guests can enjoy the tranquility of the surrounding nature while still being just a short drive away from the town's shops, restaurants, and attractions. Whether you're looking for a romantic getaway or a family vacation, Gibson Cottages is the perfect place to unwind and make lasting memories.

The Wade Cottages offer charming and cozy accommodations in the heart of Nantucket, Massachusetts. Located at 35 Shell Street, this quaint lodging option provides a peaceful and relaxing atmosphere for guests to enjoy their stay on the island. The cottages are tastefully decorated and equipped with all the amenities needed for a comfortable and enjoyable vacation. Whether you're looking for a romantic getaway or a family-friendly retreat, The Wade Cottages are the perfect choice for your stay in Nantucket.

Culdesac Cottage Bed and Breakfast is a charming lodging located at 49 Glover Square in the picturesque town of Chatham, Massachusetts. Situated in a peaceful cul-de-sac, this cozy cottage offers a serene and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The accommodations are tastefully decorated and feature modern amenities to ensure a comfortable stay. Guests can enjoy a delicious homemade breakfast each morning, served in the inviting dining area. With its convenient location near beaches, shopping, and dining options, Culdesac Cottage Bed and Breakfast is the perfect choice for a memorable stay on Cape Cod.

St. Aubin's Bayside Cottages is a charming seaside retreat located at 265 Turnip Field Road in Eastham, Massachusetts, United States. Nestled along the picturesque coastline, this institution offers cozy cottages with stunning views of the bay. Guests can relax and unwind in the peaceful surroundings, take leisurely walks along the beach, or explore the nearby attractions. With its serene atmosphere and comfortable accommodations, St. Aubin's Bayside Cottages is the perfect destination for a tranquil getaway by the sea.

Harbor Village Cottages is a charming lodging institution located at 160 Marston Avenue in Barnstable, Massachusetts, United States. Nestled in a picturesque coastal town, Harbor Village Cottages offers cozy and comfortable accommodations for guests looking to relax and unwind by the sea. Each cottage is tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy the tranquil surroundings, explore the nearby beaches and attractions, or simply take in the beautiful views of the harbor. Whether you're planning a romantic getaway or a family vacation, Harbor Village Cottages provides a peaceful retreat for all travelers.

Sunset Bluff Cottages is a charming accommodation located at 1 Knowles Heights Road in Truro, Massachusetts, United States. Nestled on a picturesque bluff overlooking the stunning sunset views of the ocean, this quaint retreat offers cozy cottages for a relaxing getaway. Each cottage is beautifully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy peaceful walks along the nearby beach, relax on their private deck with a glass of wine, or explore the charming town of Truro. With its serene atmosphere and breathtaking views, Sunset Bluff Cottages is the perfect destination for a tranquil and rejuvenating vacation.

The Summer House Cottages is a charming seaside retreat located at 17 Ocean Avenue in Siasconset, Massachusetts. This institution offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway by the ocean. The cozy cottages provide a comfortable and intimate stay, while the on-site restaurant serves delicious meals made with fresh, local ingredients. Guests can enjoy stunning views of the ocean and easy access to the beach, creating a peaceful and rejuvenating atmosphere. Whether you're looking for a romantic escape or a family vacation, The Summer House Cottages is the ideal choice for a memorable stay on the beautiful island of Nantucket.

Metter's Cottages is a charming accommodation located at 84 Chatharbor Lane in the picturesque town of Chatham, Massachusetts. Nestled in a tranquil setting, these cozy cottages offer a perfect retreat for those looking to escape the hustle and bustle of everyday life. Each cottage is beautifully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy the peaceful surroundings, relax on the private deck, or take a short stroll to the nearby beach. Metter's Cottages is the ideal choice for a relaxing getaway on Cape Cod.