TOP 30 Best Luxury vacation rentals in Massachusetts

Welcome to Herreshoff Castle, a unique and enchanting destination nestled in the heart of Marblehead, Massachusetts. Located at 2 Crocker Park Lane, our historic castle offers a captivating blend of old-world charm and modern comforts, making it a perfect getaway for history enthusiasts, architecture admirers, and those seeking a distinctive experience. Originally built in the early 20th century, Herreshoff Castle is a stunning replica of a medieval European castle, complete with stone walls, turrets, and a picturesque courtyard. The castle is steeped in history, with each room telling a story of its rich past and the fascinating individuals who have called it home.

RentNoho.com is a premier real estate agency located in the heart of Northampton, Massachusetts. Our team of experienced professionals is dedicated to helping clients find the perfect rental property that suits their needs and lifestyle. Whether you are looking for a cozy apartment, a spacious house, or a trendy loft, RentNoho.com has a diverse selection of properties to choose from. Our convenient location at 19 Hawley Street makes it easy for clients to stop by and discuss their rental needs with our friendly staff. Let RentNoho.com help you find your next home in Northampton!

The Summer House India Street is a charming lodging institution located at 31 India Street in the picturesque town of Nantucket, Massachusetts. Situated in a historic building, this cozy retreat offers guests a peaceful and relaxing atmosphere for their summer getaway. With comfortable accommodations and a convenient location near the island's attractions, The Summer House India Street is the perfect choice for those looking to experience the beauty of Nantucket. Immerse yourself in the island's rich history and natural beauty while staying at this lovely establishment.

The Summer House Fair Street is a charming lodging institution located at 27 Fair Street in the picturesque town of Nantucket, Massachusetts. This historic establishment offers a cozy and inviting atmosphere for guests looking to experience the beauty and tranquility of the island. With comfortable accommodations, friendly staff, and a convenient location near the beach and downtown area, The Summer House Fair Street is the perfect choice for a relaxing getaway on Nantucket. Whether you're looking for a romantic retreat or a family vacation, this charming inn has everything you need for a memorable stay.

Welcome to 5-33 Modern Private Studio in the heart of Boston, Massachusetts! Our stylish and contemporary private studio awaits you for a comfortable and convenient stay. Located at 5 Cortes Street, our lodging is the perfect choice for travelers looking for a modern and relaxing accommodation option. With top-notch amenities and a prime location, you'll feel right at home during your stay with us. Book your stay at 5-33 Modern Private Studio today and experience the best of Boston!

One Newport is a dynamic institution located at 1 Newport Avenue in Quincy, Massachusetts. This innovative organization is dedicated to serving the community by providing a wide range of services and programs aimed at improving the quality of life for residents of all ages. From educational classes and workshops to recreational activities and community events, One Newport is committed to fostering a sense of unity and wellbeing in the local area. With a team of dedicated staff members and volunteers, this institution strives to create a welcoming and inclusive environment where individuals can come together to learn, grow, and connect with one another. Whether you're looking to expand your knowledge, meet new people, or simply have fun, One Newport has something for everyone. Visit us today and see how we can make a difference in your life and the community.

Kinlin Grover Real Estate is a trusted and reputable real estate agency located at 345 Front Street in Marion, Massachusetts. With a team of experienced and dedicated agents, Kinlin Grover is committed to helping clients buy, sell, and rent properties in the beautiful coastal town of Marion and beyond. Whether you are looking for a waterfront home, a charming cottage, or a luxury estate, Kinlin Grover Real Estate has the expertise and resources to assist you every step of the way. Contact them today to start your real estate journey in Marion, Massachusetts.

Bluebird Suites offers luxurious and fully furnished lodging in the heart of Boston, Massachusetts. Located at 380 Riverway, our stylish suites provide a comfortable and convenient stay for both short and long-term visitors. With modern amenities and a prime location, Bluebird Suites is the perfect choice for travelers looking for a home away from home in the bustling city of Boston.

Welcome to Tzell New England Affiliate, your premier car rental and travel agency conveniently located at 1 Appleton Street, Boston, Massachusetts. Nestled in the heart of Boston, we are dedicated to providing exceptional travel solutions tailored to meet your unique needs. Whether you're planning a business trip, a family vacation, or a weekend getaway, our experienced team is here to ensure your journey is seamless and memorable. At Tzell New England Affiliate, we offer a wide range of high-quality rental vehicles to suit every traveler's preference and budget. From compact cars to luxury SUVs, our fleet is meticulously maintained to ensure a safe and comfortable driving experience. Our flexible rental options and competitive pricing make it easy for you to explore Boston and beyond at your own pace.

Welcome to Oak Hills, your ideal destination for a relaxing getaway in Attleboro, Massachusetts. Nestled in a serene natural setting at 124 Compton Drive, Oak Hills offers a perfect blend of comfort and adventure for both short-term visitors and long-term guests. Our unique property serves as both a cozy lodging facility and an inviting RV park, catering to travelers seeking a peaceful retreat and outdoor enthusiasts alike. At Oak Hills, we pride ourselves on providing exceptional hospitality and a welcoming atmosphere. Our well-appointed accommodations ensure a comfortable stay, whether you choose to unwind in one of our charming guest rooms or park your RV in our spacious and scenic grounds. With a range of amenities designed to enhance your experience, you can enjoy the tranquility of nature without sacrificing modern conveniences.

CP Property Group is a reputable real estate agency located at 672 Chestnut Street in Springfield, Massachusetts, United States. With a team of experienced and dedicated professionals, CP Property Group specializes in buying, selling, and renting residential and commercial properties in the local area. Whether you are looking for your dream home, a new office space, or an investment property, CP Property Group is committed to providing top-notch service and expertise to help you achieve your real estate goals. Contact us today to learn more about how we can assist you with all of your real estate needs.

Whaleback Hill Cottages is a charming lodging institution located in the picturesque town of Sandwich, Massachusetts. Nestled on a scenic hilltop overlooking the historic Route 6A, this cozy retreat offers a peaceful and relaxing getaway for guests looking to unwind and rejuvenate. The cottages are beautifully appointed with modern amenities and rustic charm, providing a comfortable and inviting atmosphere for visitors. Whether you're seeking a romantic escape, a family vacation, or a solo retreat, Whaleback Hill Cottages is the perfect destination for your next stay in Cape Cod.

Stone House Properties LLC is a reputable real estate agency located in Pittsfield, Massachusetts, United States. Specializing in buying, selling, and renting residential properties, our experienced team of professionals is dedicated to providing top-notch services to our clients. Whether you are looking for a cozy starter home or a luxurious estate, we have the expertise to help you find the perfect property to suit your needs. With a focus on customer satisfaction and attention to detail, Stone House Properties LLC is the go-to agency for all your real estate needs in the Pittsfield area.

Blue Bay Real Estate Inc is a reputable real estate agency located at 359 Commercial Street in the charming town of Provincetown, Massachusetts. With a team of experienced and knowledgeable agents, we specialize in helping clients buy, sell, and rent properties in this picturesque coastal community. Whether you're searching for a vacation home, investment property, or your forever home, our dedicated team is here to assist you every step of the way. Contact us today to learn more about how we can help you achieve your real estate goals in Provincetown.

The Harwich Haven is a reputable real estate and travel agency located at 81 Division Street in the charming town of Harwich, Massachusetts, United States. With a team of experienced professionals, The Harwich Haven specializes in helping clients find their dream homes in this picturesque coastal community, as well as assisting with all their travel needs. Whether you are looking to buy or rent a property, or plan the perfect vacation getaway, The Harwich Haven is dedicated to providing top-notch service and expertise to make your real estate and travel experience a smooth and enjoyable one. Visit us today and let us help you find your own piece of paradise in Harwich.

Kinlin Grover Compass Real Estate is a reputable real estate agency located in Truro, Massachusetts. With a prime location on U.S. 6, they offer expert services in buying, selling, and renting properties in the area. Their team of experienced agents is dedicated to helping clients navigate the real estate market with ease and confidence. Whether you are looking for a vacation home, investment property, or permanent residence, Kinlin Grover Compass Real Estate has the knowledge and resources to assist you every step of the way. Trust in their expertise and local insight to find your dream property in beautiful Truro, Massachusetts.

United Travel Inc is a premier travel agency located at 2500 Main Street in Tewksbury, Massachusetts. 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 have the knowledge and resources to make your dream vacation a reality. Contact us today to start planning your next unforgettable travel experience with United Travel Inc.

Upper Cape & Vineyard Realty is a premier real estate agency located in Tisbury, Massachusetts, United States. Specializing in properties on Cape Cod and Martha's Vineyard, our team of experienced agents are dedicated to helping clients find their dream homes or investment properties in these beautiful coastal regions. Whether you're looking for a beachfront cottage, a historic home, or a luxury estate, Upper Cape & Vineyard Realty is committed to providing personalized service and expert guidance throughout the buying or selling process. Contact us today to start your real estate journey with us.

Corbin Norton House is a charming bed and breakfast located at 87 Ocean Avenue in Oak Bluffs, Massachusetts. This historic institution offers comfortable accommodations in a picturesque setting just steps away from the beach. Guests can enjoy beautifully decorated rooms, delicious breakfasts, and personalized service during their stay. With its convenient location and warm hospitality, Corbin Norton House is the perfect destination for a relaxing getaway on Martha's Vineyard.

Welcome to Highwood Manor House, your quintessential retreat nestled in the heart of the Berkshires in Stockbridge, Massachusetts. Located at 01240, our historic manor offers a unique blend of timeless elegance and modern comfort, providing an idyllic setting for a relaxing getaway. Step into a world of charm and sophistication as you explore our beautifully appointed rooms, each thoughtfully designed to capture the essence of the manor's storied past while offering all the contemporary amenities you desire. Whether you're enjoying the tranquility of our lush gardens, savoring a gourmet breakfast in our sunlit dining room, or unwinding by the fireplace in our cozy lounge, Highwood Manor House promises an unforgettable experience.

Brook Cove is a charming lodging institution located at 30 Linda Lane in the picturesque town of Great Barrington, Massachusetts. Surrounded by lush greenery and peaceful surroundings, Brook Cove offers a serene retreat for guests looking to escape the hustle and bustle of city life. The cozy accommodations and warm hospitality make it the perfect destination for a relaxing getaway. Whether you're looking to explore the beautiful Berkshires or simply unwind in nature, Brook Cove provides a tranquil and comfortable stay for all visitors.

River Inn is a charming lodging establishment nestled in the heart of Springfield, Massachusetts. Located in the United States, this cozy inn offers comfortable accommodations and a warm, inviting atmosphere for guests to relax and unwind. With a picturesque setting along the river, guests can enjoy scenic views and a peaceful environment. Whether you are traveling for business or leisure, River Inn provides a convenient and welcoming place to stay during your time in Springfield.

Manor Lane is a charming institution located at 145 Hurlburt Road in Great Barrington, Massachusetts. This real estate and travel agency offers a unique rental home with French elegance in the tranquil Berkshire mountains. The private 4 bedroom, 4 bath home is the perfect vacation rental, just 5 minutes away from the town of Great Barrington. Escape to this one-of-a-kind Berkshire vacation rental for a summer getaway or holiday retreat. Immerse yourself in the beauty of the Berkshire mountains while enjoying all that Great Barrington has to offer. Experience the best of both worlds at Manor Lane, where luxury meets relaxation in the heart of Massachusetts.

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.

Holiday Apartments is a charming accommodation located at 37 River Street in West Springfield, Massachusetts. Our apartments offer a cozy and comfortable space for visitors looking for a home away from home during their holiday. With a convenient location near local attractions and amenities, Holiday Apartments is the perfect choice for travelers seeking a relaxing and enjoyable stay in the United States. Whether you are visiting for business or pleasure, our apartments provide all the comforts and conveniences you need for a memorable stay. Book your stay with us today and experience the warmth and hospitality of Holiday Apartments.

Castle Cove Villa is a luxurious real estate and travel agency located at 202 Killdeer Road in Webster, Massachusetts. Our stunning villa offers a unique and unforgettable experience for those seeking a peaceful and relaxing getaway. Situated in a picturesque location, our villa boasts breathtaking views of the surrounding landscape and a tranquil atmosphere that is perfect for unwinding and rejuvenating. Whether you are looking to purchase a dream vacation home or book a memorable holiday rental, Castle Cove Villa is here to make your travel dreams a reality. Contact us today to start planning your next unforgettable escape.

Blue Hill Retreat is a premier destination located at 212 Blue Hill Road in the picturesque town of Great Barrington, Massachusetts. As a unique institution offering both real estate and travel services, Blue Hill Retreat provides a one-of-a-kind experience for those looking to escape the hustle and bustle of everyday life. Whether you are searching for your dream vacation rental or looking to purchase a tranquil getaway property, our team of experts is dedicated to helping you find the perfect retreat. With a focus on luxury and relaxation, Blue Hill Retreat is the ideal choice for those seeking a peaceful and rejuvenating experience.

The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.

Pride Travel Inc is a premier travel agency located at 51 Kings Lane in Springfield, Massachusetts. Our dedicated team of experienced travel professionals is committed to providing exceptional service and personalized travel experiences for our clients. Whether you're planning a family vacation, romantic getaway, or business trip, Pride Travel Inc is here to help you every step of the way. We offer a wide range of travel services including flight bookings, hotel accommodations, car rentals, and vacation packages. Contact us today to start planning your next adventure with Pride Travel Inc.

Carbuncle Beach House is a charming park located at 12 Carbuncle Drive in Oxford, Massachusetts, United States. This serene and picturesque institution offers a peaceful retreat for visitors looking to escape the hustle and bustle of everyday life. With its beautiful beachfront setting and lush green surroundings, Carbuncle Beach House is the perfect place to relax, unwind, and connect with nature. Whether you're looking to enjoy a leisurely stroll along the shoreline, have a picnic with loved ones, or simply soak up the sun, Carbuncle Beach House provides a tranquil and rejuvenating experience for all who visit.