TOP 30 Best Luxury vacation villas in Massachusetts

Three Dogs Villa is a charming lodging establishment located in Middleborough, Massachusetts. Situated at 364 Marion Road, this cozy retreat offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The villa is pet-friendly, welcoming furry friends of all shapes and sizes to join their owners on a memorable stay. With comfortable accommodations and personalized service, Three Dogs Villa is the perfect destination for a weekend getaway or a longer vacation. Enjoy the serene surroundings and make unforgettable memories at this delightful institution.

Villa Sofia is a charming restaurant located at 17 Main Street in Brimfield, Massachusetts. Known for its delicious and authentic cuisine, Villa Sofia offers a cozy and welcoming atmosphere for guests to enjoy a memorable dining experience. With a menu featuring a variety of Italian dishes made with fresh, high-quality ingredients, Villa Sofia is a popular choice for both locals and visitors alike. Whether you're looking for a casual meal with friends or a romantic dinner for two, Villa Sofia is the perfect spot to satisfy your cravings for delicious food in a warm and inviting setting.

The Villa is a charming and cozy restaurant located at 239 Maple Street in Middleton, Massachusetts. Known for its delicious Italian cuisine and warm hospitality, The Villa offers a unique dining experience for guests of all ages. Whether you're looking for a romantic date night or a casual meal with friends and family, The Villa is the perfect spot to enjoy a taste of Italy right in the heart of Middleton. Come and indulge in our mouth-watering dishes, made with fresh and locally sourced ingredients, and experience the inviting atmosphere that keeps our patrons coming back for more. Join us at The Villa for a culinary journey that will leave you satisfied and craving for more.

COLBYCO Vacation and Short Term Rental Property Management is a premier real estate and travel agency located at 93 Dresser Street in Boston, Massachusetts. We specialize in managing vacation and short term rental properties, ensuring that guests have a seamless and enjoyable experience during their stay. Our team is dedicated to providing top-notch customer service and helping property owners maximize their rental income. Whether you're looking for a cozy cabin in the mountains or a luxury beachfront villa, COLBYCO has the perfect property for your next getaway. Book with us today and experience the ultimate in vacation rental management.

High Pocket Vacation Rental is a charming lodging located at 38 Adams Place in the picturesque town of Colrain, Massachusetts, United States. Nestled in a serene and peaceful setting, this vacation rental offers a cozy and comfortable stay for guests looking to escape the hustle and bustle of everyday life. With well-appointed accommodations and a range of amenities, High Pocket Vacation Rental is the perfect home away from home for your next getaway. Whether you're looking to relax and unwind or explore the beautiful surroundings, this institution provides a welcoming and inviting atmosphere for all visitors.

MV Cloud House Vacation Rental is a premier real estate and travel agency located in the picturesque town of Tisbury, Massachusetts. Our agency specializes in providing luxurious vacation rental properties for those looking to experience the beauty of Martha's Vineyard. Nestled at 36 Burts Way, our properties offer stunning views, top-notch amenities, and unparalleled customer service. Whether you are looking for a cozy cottage for a romantic getaway or a spacious beachfront villa for a family vacation, MV Cloud House Vacation Rental has the perfect property for you. Book your dream vacation today and let us help you create memories that will last a lifetime.

Villa Fiori is a charming lodging located at 218 Summer Street in the picturesque town of Manchester-by-the-Sea, Massachusetts. This cozy retreat offers a peaceful atmosphere surrounded by beautiful gardens and stunning views. Guests can relax in comfortable rooms, enjoy delicious meals in the on-site restaurant, and take advantage of nearby attractions such as the beach and shopping districts. Whether you are looking for a romantic getaway or a relaxing vacation, Villa Fiori provides the perfect setting for a memorable stay.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located in Wellfleet, Massachusetts. With a prime location on U.S. 6, this institution offers a wide range of vacation rental properties for those looking to explore the charming town of Wellfleet and the surrounding areas. Whether you are seeking a beachfront cottage, a cozy cabin in the woods, or a luxurious waterfront villa, Kinlin Grover Vacation Rentals has the perfect accommodation for your getaway. Their team of experienced agents are dedicated to providing top-notch customer service and ensuring that your vacation experience is seamless and unforgettable. Contact Kinlin Grover Vacation Rentals today to start planning your dream vacation on Cape Cod.

Italian Exclusive Vacation is a premier travel agency located in Waltham, Massachusetts, specializing in creating luxurious and unforgettable vacations to Italy. Our team of experienced travel experts is dedicated to crafting personalized itineraries that cater to the unique preferences and interests of each client. From exploring the historic streets of Rome to savoring the finest wines in Tuscany, we ensure that every aspect of your Italian getaway is meticulously planned and executed. Whether you seek a romantic honeymoon, a family adventure, or a solo retreat, Italian Exclusive Vacation is your gateway to experiencing the beauty, culture, and cuisine of Italy in style and comfort. Visit us at 24 Crescent Street to start planning your dream vacation today.

Pangea Luxury Travel is a premier travel agency located in Newburyport, Massachusetts, specializing in creating unforgettable travel experiences for clients. With a team of experienced travel experts who have explored all 7 continents, Pangea Luxury Travel is dedicated to helping clients discover the wonders of the world. At Pangea Luxury Travel, we believe in the power of personalized service and take the time to understand our clients' unique travel needs and desires. Whether you're seeking a luxurious beach getaway, a cultural exploration, or an adventurous safari, we are here to curate the perfect itinerary for you and your family.

BKG Vacation Rentals is a premier real estate and travel agency located at 313 Wareham Road in Marion, Massachusetts, United States. We specialize in providing top-quality vacation rental properties for travelers looking to experience the beauty and charm of the Massachusetts coastline. Our experienced team is dedicated to helping clients find the perfect rental property for their vacation needs, whether it be a cozy beach cottage or a luxurious waterfront estate. With a wide range of properties to choose from, BKG Vacation Rentals is your go-to destination for a memorable and stress-free vacation experience. Contact us today to start planning your next getaway!

Cape Cod Villa is a prestigious real estate and travel agency located at 16 Olde Coach Lane in Harwich, Massachusetts. Specializing in luxurious vacation rentals and properties for sale on Cape Cod, our team of experienced agents are dedicated to helping clients find their dream home or perfect vacation getaway. With a focus on personalized service and attention to detail, Cape Cod Villa is the go-to destination for those seeking a memorable experience on the beautiful Cape Cod peninsula. Contact us today to start your journey towards owning a piece of paradise or planning your next unforgettable vacation.

Karen M. Overtoom Real Estate and Vacation Rentals is a premier real estate and travel agency located in the picturesque town of West Tisbury, Massachusetts. With a prime location at 33 Scotchmans Lane, this institution offers a wide range of services to help clients find their dream vacation rental or perfect property. Whether you're looking for a cozy cabin in the woods or a luxurious beachfront villa, the experienced team at Karen M. Overtoom Real Estate and Vacation Rentals is dedicated to helping you find the perfect getaway. With their knowledge of the local area and commitment to customer satisfaction, you can trust that you're in good hands when working with this reputable agency. Experience the beauty of Martha's Vineyard with the help of Karen M. Overtoom Real Estate and Vacation Rentals.

Seascape Vacation Rental Cape Cod is a premier real estate and travel agency located at 253 Old Wharf Road in Dennis, Massachusetts. Offering a wide selection of vacation rental properties in the picturesque Cape Cod area, Seascape is dedicated to providing guests with a memorable and relaxing getaway experience. With stunning ocean views, luxurious accommodations, and top-notch customer service, Seascape Vacation Rental Cape Cod is the perfect choice for those looking to escape the hustle and bustle of everyday life and immerse themselves in the natural beauty of the Cape Cod region. Book your dream vacation with Seascape today and create lasting memories that will last a lifetime.

Parker Villas is a reputable real estate and travel agency located in Beverly, Massachusetts, United States. Specializing in luxury villa rentals in Europe, Parker Villas offers a seamless booking process and excellent communication with hosts. Guests have enjoyed their stays in locations such as Ravello and Napoli, with smooth check-in and checkout experiences. Whether you're looking for a relaxing seaside retreat or a cultural city break, Parker Villas is the perfect choice for your next European holiday.

Mews 5A Pool Villa Condo Trust is a luxurious and exclusive condominium located at 100 Mid-Iron Way in Mashpee, Massachusetts. This stunning property offers a serene and upscale living experience with a beautiful pool and villa setting. The trust is committed to providing residents with a high-quality living environment and exceptional amenities. Whether you are looking for a peaceful retreat or a place to entertain guests, Mews 5A Pool Villa Condo Trust is the perfect place to call home.

Five Star Vacation Rental is a premier real estate and travel agency located at 183 North Shore Boulevard in Sandwich, Massachusetts. We specialize in providing luxurious vacation rental properties in the United States. Our properties are meticulously selected to ensure the highest quality and comfort for our guests. Whether you are looking for a beachfront villa, a cozy mountain cabin, or a chic urban apartment, we have the perfect accommodation for your dream vacation. With our five-star service and attention to detail, we strive to make your vacation experience truly unforgettable. Book with Five Star Vacation Rental for a truly exceptional getaway.

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.

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.

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.

Cape Cod Vacation Rentals is a reputable real estate and travel agency located at 33 Bradford Street in Concord, Massachusetts. Specializing in providing high-quality vacation rental properties in the picturesque Cape Cod area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're looking for a cozy beachfront cottage or a spacious luxury villa, our team of experienced agents is dedicated to helping you find the perfect vacation rental for your next getaway. With personalized service and attention to detail, Cape Cod Vacation Rentals is your go-to destination for a memorable and relaxing vacation experience on the beautiful shores of Cape Cod.

Kinlin Grover Vacation Rentals is a premier real estate and travel agency located at 4 Wianno Avenue in Barnstable, Massachusetts, United States. With a reputation for excellence in the vacation rental industry, Kinlin Grover offers a wide range of luxury properties for rent in the beautiful Cape Cod area. Whether you're looking for a beachfront villa, a cozy cottage, or a spacious family home, Kinlin Grover has the perfect vacation rental for you. Their team of experienced agents is dedicated to helping you find the ideal accommodation for your next getaway, ensuring a memorable and stress-free vacation experience. Experience the best of Cape Cod with Kinlin Grover Vacation Rentals.

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.

Cape Cod Homes Vacation is a reputable real estate agency located at 109 Pawkannawkut Drive in Yarmouth, Massachusetts. We specialize in providing vacation rental homes on Cape Cod, offering a wide selection of properties to suit every traveler's needs and preferences. Whether you are looking for a cozy cottage by the beach or a spacious family home with stunning views, our experienced team is dedicated to helping you find the perfect vacation rental for your stay on Cape Cod. With our personalized service and attention to detail, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream Cape Cod getaway!

Luxury Travel Agency - Elite Estates Greek Villas is a prestigious institution located at 59 Rebecca Road in Scituate, Massachusetts, United States. Specializing in both real estate and travel services, this agency offers exquisite Greek villas for the elite traveler seeking a luxurious and unforgettable vacation experience. With a focus on quality, exclusivity, and personalized service, Elite Estates Greek Villas caters to discerning clients looking for a truly exceptional getaway in the beautiful country of Greece. Whether you are searching for a stunning property to invest in or seeking a bespoke travel package, this agency is dedicated to exceeding your expectations and creating unforgettable memories.

Luxury Travel is a premier travel agency located at 15 Lee Street in Marblehead, Massachusetts, United States. Specializing in providing top-notch, personalized travel experiences for discerning clients, Luxury Travel offers a wide range of luxurious vacation packages, exclusive accommodations, and VIP services. With a team of experienced travel experts, Luxury Travel is dedicated to creating unforgettable journeys tailored to each client's unique preferences and desires. Whether you're seeking a lavish beach getaway, a private yacht charter, or a custom-tailored itinerary to a dream destination, Luxury Travel is your go-to agency for all things luxury travel. Book your next extraordinary adventure with Luxury Travel and experience the ultimate in luxury travel experiences.

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.

LuxuryOnly Cruises is a premier travel agency located at 100 Quannapowitt Parkway in Wakefield, Massachusetts, United States. Specializing in luxury cruise vacations, we offer a wide range of exclusive cruise packages to some of the most exotic and breathtaking destinations around the world. Our experienced and knowledgeable travel advisors are dedicated to providing top-notch service and creating unforgettable experiences for our clients. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, LuxuryOnly Cruises has the perfect cruise package for you. Book your dream vacation with us today and set sail on a luxury cruise experience like no other.

Days Cottages Condominiums is a historic colony of iconic cottages located at 276 Shore Road in Truro, Massachusetts, United States. This charming resort is not only a popular tourist attraction but also a beloved destination for generations of guests. The cottages have been featured in film, artwork, and photography, making them a truly iconic part of the local landscape. With their picturesque setting and cozy accommodations, Days Cottages Condominiums offer a unique and unforgettable vacation experience.