TOP 30 Luxury vacation getaway rentals in Massachusetts

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Welcome to Berkshire Rental Properties, located at 29 Benton Avenue in Great Barrington, Massachusetts. Whether you're in search of a quaint cottage or a luxurious multifamily estate, Berkshire Rental Properties offers a wide range of options to suit your needs. Our listings are carefully selected for their desirability, location, and top-notch amenities, providing a step above the typical rental offerings. At Berkshire Rental Properties, we understand the allure of the Berkshires and aim to provide a seamless getaway experience for our guests. Whether you're seeking outdoor adventures, cultural experiences, or simply a relaxing retreat, our properties serve as the perfect gateway to all that the Berkshires have to offer.

Grieshaber's Getaway is a premier travel agency located at 60 Sutton Place in East Longmeadow, Massachusetts. We specialize in creating unforgettable travel experiences for our clients, offering a wide range of services including booking flights, accommodations, and activities. Our team of experienced travel experts is dedicated to providing personalized service and expert advice to help you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, a thrilling adventure, or a romantic escape, Grieshaber's Getaway has you covered. Contact us today to start planning your dream vacation!

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.

Del Mar Vacations is a well-established real estate and travel agency located in Orleans, Massachusetts. Specializing in vacation rentals and property management, our dedicated team is committed to providing top-notch service to clients looking to explore the beautiful Cape Cod area. Whether you're looking for a cozy beachfront cottage or a luxurious waterfront home, Del Mar Vacations has a wide range of properties to suit every taste and budget. With our expert knowledge of the area and personalized approach, we strive to make your vacation experience unforgettable. Visit us at 24 South Orleans Road to start planning your dream getaway today.

Nantucket Rentals is a premier real estate and travel agency located at 53 Main Street in Nantucket, Massachusetts. We specialize in providing luxurious vacation rentals on the picturesque island of Nantucket. Our team of experienced agents will help you find the perfect rental property for your next getaway, whether you're looking for a cozy cottage by the beach or a spacious waterfront estate. With our local expertise and personalized service, we ensure that your Nantucket vacation is unforgettable. Contact us today to start planning your dream vacation on this charming island.

Martha's Vineyard Rentals is a reputable real estate and travel agency located at 13 Beach Street Extension in Tisbury, Massachusetts. Specializing in vacation rentals on the picturesque Martha's Vineyard island, this agency offers a wide range of properties to suit every traveler's needs. Whether you're looking for a cozy cottage by the beach or a luxurious waterfront estate, Martha's Vineyard Rentals has something for everyone. With personalized service and attention to detail, they strive to make your vacation experience unforgettable. Book your dream getaway with Martha's Vineyard Rentals today and start planning your perfect island escape.

Waterfront Rentals is a premier real estate and travel agency located at 411 Massachusetts 28 in Yarmouth, Massachusetts. Specializing in luxurious waterfront properties, our agency offers a wide range of rental options for those looking to enjoy the beauty of Cape Cod's stunning coastlines. Whether you're seeking a peaceful retreat or a fun-filled vacation, our experienced team is dedicated to helping you find the perfect rental for your needs. With top-notch customer service and a diverse selection of properties, Waterfront Rentals is your go-to destination for an unforgettable stay on the shores of Massachusetts.

Vacation Village in the Berkshires is a charming lodging institution located at 276 Brodie Mountain Road in Hancock, Massachusetts, United States. Nestled in the picturesque Berkshires region, this resort offers cozy accommodations and top-notch amenities for a relaxing and enjoyable vacation experience. Guests can unwind in spacious suites equipped with modern comforts, take a dip in the indoor or outdoor pools, or explore the nearby attractions such as ski slopes, hiking trails, and cultural venues. Whether you're seeking a romantic getaway or a fun family vacation, Vacation Village in the Berkshires is the perfect destination for your next trip.

Gloucester House Rental - Belle View is a charming lodging establishment located at 57 Grapevine Road in Gloucester, Massachusetts, United States. As a real estate and travel agency, we specialize in providing luxurious house rentals with breathtaking views of the surrounding area. Our properties are meticulously maintained and offer all the amenities needed for a comfortable and relaxing stay. Whether you are looking for a weekend getaway or a longer vacation, Gloucester House Rental - Belle View is the perfect choice for your next trip to Gloucester.

Sea Breeze Inn beach rentals is a charming lodging located at 270 Ocean Avenue in Barnstable, Massachusetts, United States. Situated near the beautiful coastline, this institution offers cozy and comfortable accommodations for guests looking to enjoy a relaxing beach getaway. With a serene atmosphere and stunning ocean views, Sea Breeze Inn is the perfect destination for those seeking a peaceful retreat by the sea. Whether you're looking to unwind on the beach, explore the nearby attractions, or simply relax in the comfort of your room, Sea Breeze Inn beach rentals provides a warm and welcoming stay for all visitors.

Located in the picturesque town of Mashpee, Massachusetts, Mashpee Luxury Condos Royal Holidays offers a luxurious lodging experience like no other. Situated at 30 4 Seasons Drive, our elegant condos are the perfect choice for a relaxing getaway or a romantic retreat. With top-notch amenities, stunning views, and impeccable service, our institution provides a truly royal holiday experience. Whether you're looking to explore the nearby beaches, golf courses, or shopping destinations, our prime location makes it easy to enjoy all that Mashpee has to offer. Book your stay with us and indulge in the ultimate luxury vacation.

Bluegreen Vacations The Soundings, Ascend Resort Collection is a charming lodging institution located at 79 Chase Avenue in Dennis, Massachusetts, United States. Situated right on the beautiful shores of Cape Cod, this resort offers guests a peaceful and picturesque getaway. The accommodations are spacious and comfortable, with modern amenities and stunning views of the ocean. Guests can relax by the outdoor pool, take a stroll along the beach, or explore the nearby attractions such as museums, shops, and restaurants. Whether you're looking for a romantic retreat or a fun family vacation, Bluegreen Vacations The Soundings is the perfect destination.

My Cape Cod Vacation Home is a coastal retreat located in Dennis Port, Massachusetts, offering a peaceful getaway on beautiful Cape Cod. Our lodging establishment features 5 uniquely designed guest rooms, each providing a tranquil environment for a restful night's sleep. Situated within walking distance to the beach, guests can enjoy the sun, sand, and surf just moments away. Additionally, our property boasts a cozy fire pit for evening relaxation and central air conditioning for ultimate comfort. Whether you're looking for a relaxing beach vacation or a convenient home base for exploring all that Cape Cod has to offer, My Cape Cod Vacation Home is the perfect choice.

Near Beach Rentals is a cozy lodging option located at 183 Captain Chase Road in Dennis, Massachusetts. Just a stone's throw away from the beach, this institution offers comfortable accommodations for those looking to enjoy a relaxing getaway by the sea. Whether you're looking for a romantic escape or a fun-filled family vacation, Near Beach Rentals provides the perfect home base for your coastal adventures. With its convenient location and charming atmosphere, this institution is the ideal choice for travelers seeking a peaceful retreat near the shore.

Beachcombers Vacation Rentals and Real Estate Sales is a premier real estate and travel agency located in Aquinnah, Massachusetts. Situated at 10 Old South Road, this institution offers a wide range of vacation rentals and properties for sale in this picturesque coastal town. Whether you are looking for a dream vacation rental or interested in purchasing your own piece of paradise, Beachcombers Vacation Rentals and Real Estate Sales has the expertise and resources to help you find the perfect property. With a team of experienced agents and a commitment to exceptional customer service, Beachcombers is your go-to destination for all your real estate and vacation rental needs in Aquinnah, Massachusetts.

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.

Martha's Vineyard Vacation Rentals & Real Estate is a premier real estate and travel agency located at 107 Beach Road in Tisbury, Massachusetts, United States. Specializing in luxury vacation rentals and real estate properties on the beautiful Martha's Vineyard island, our dedicated team is committed to providing exceptional service and helping clients find their perfect getaway or dream home. Whether you are looking for a relaxing vacation rental or interested in investing in property on the island, Martha's Vineyard Vacation Rentals & Real Estate has the expertise and resources to make your experience unforgettable. Contact us today to start planning your Martha's Vineyard escape!

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.

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.

Gateway Getaway is a premier real estate agency located at 123 Packard Street in the picturesque town of Plymouth, Massachusetts. Our dedicated team of professionals is committed to helping clients find their dream homes or investment properties in this charming coastal community. Whether you're looking for a beachfront retreat, a historic colonial, or a cozy cottage, Gateway Getaway has the expertise and resources to make your real estate dreams a reality. Contact us today to start your journey towards finding the perfect gateway to your new life in Plymouth.

Beach Side Rental is a premier real estate and travel agency located at 14 Wildwood Avenue in Wareham, Massachusetts. We specialize in providing top-quality rental properties near the beautiful beaches of Massachusetts. Whether you are looking for a cozy cottage for a romantic getaway or a spacious beach house for a family vacation, we have the perfect rental for you. Our friendly and knowledgeable staff are dedicated to helping you find the ideal property to make your beach vacation unforgettable. Contact us today to start planning your next beachside getaway!

East Sandwich Luxury Vacation Rental is a premier real estate agency located at 11 Fort Hill Road in the charming town of Sandwich, Massachusetts. Our agency specializes in offering luxurious vacation rentals in the East Sandwich area, providing guests with top-notch accommodations and exceptional service. Whether you are looking for a beachfront property, a cozy cottage, or a spacious family home, we have a wide selection of rental options to choose from. With stunning views, upscale amenities, and a prime location near the beach, our vacation rentals are the perfect choice for a memorable getaway on Cape Cod. Book your stay with East Sandwich Luxury Vacation Rental and experience the ultimate in relaxation and comfort.

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.

Property Cape Cod Vacation Rentals is a premier real estate and travel agency located in the heart of Barnstable, Massachusetts. We specialize in providing top-notch vacation rental properties on the beautiful Cape Cod peninsula. Our dedicated team of professionals is committed to helping you find the perfect rental for your next getaway, whether you're looking for a cozy beach cottage or a luxurious waterfront estate. With our extensive knowledge of the area and personalized service, we strive to make your vacation experience unforgettable. Contact us today to start planning your dream Cape Cod vacation!

The Laurel Cape Cod Vacation Rental is a charming property located at 3 Laurel Lane in Truro, Massachusetts. This beautifully appointed vacation rental is managed by a reputable real estate and travel agency, offering guests a unique and memorable experience on Cape Cod. With its prime location and comfortable accommodations, The Laurel is the perfect destination for those looking to relax and unwind on the picturesque shores of Cape Cod. Whether you're seeking a romantic getaway or a family vacation, The Laurel Cape Cod Vacation Rental is the ideal choice for your next escape.

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 in Truro, Massachusetts. Situated at 314 U.S. 6, this institution offers a wide range of vacation rental properties for those looking to explore the beautiful Cape Cod area. Whether you're seeking a beachfront cottage, a cozy cabin in the woods, or a luxurious waterfront estate, Kinlin Grover has the perfect accommodation for your getaway. With exceptional customer service and a knowledgeable staff, you can trust Kinlin Grover Vacation Rentals to help you plan an unforgettable vacation experience.

Cape House Rental is a reputable real estate agency located at 42 Seaside Avenue in Dennis, Massachusetts, United States. Specializing in rental properties in the beautiful Cape Cod area, our agency offers a wide selection of vacation homes, cottages, and beachfront properties for short-term and long-term stays. With personalized service and a team of experienced agents, Cape House Rental is dedicated to helping clients find the perfect home away from home for their next getaway. Experience the charm and beauty of Cape Cod with Cape House Rental.

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.

Experience the ultimate vacation getaway at our luxurious 3-bedroom condo rental located at Ocean Edge Resort in Brewster, Massachusetts. Nestled in a serene and picturesque setting, this spacious accommodation offers all the comforts of home with the added bonus of resort amenities. Enjoy easy access to the beach, golf courses, tennis courts, and more. Whether you're looking for a relaxing retreat or an action-packed adventure, our condo rental at Ocean Edge Resort is the perfect choice for your next vacation. Book your stay today at 34 Endicott Lane and make unforgettable memories in the heart of Cape Cod.