TOP 30 Vacation house rentals in Massachusetts

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TOURISTS is a unique lodging institution located at 915 State Road in North Adams, Massachusetts. Situated in the scenic Berkshires region of the United States, TOURISTS offers a one-of-a-kind experience for travelers looking to immerse themselves in nature and art. The institution provides a range of accommodations, from cozy cabins to stylish rooms, all designed with a modern and minimalist aesthetic. Guests can enjoy amenities such as a communal kitchen, outdoor fire pits, and access to hiking trails. Whether you're seeking a peaceful retreat or a cultural adventure, TOURISTS is the perfect destination for your next getaway.

American Homes and Rentals LLC is a reputable real estate agency located at 700 Main Street in Great Barrington, Massachusetts. We specialize in helping clients find their dream homes or rental properties in the beautiful and vibrant area of Great Barrington. With a team of experienced and dedicated real estate professionals, we provide top-notch services to ensure a smooth and stress-free real estate experience for our clients. Whether you are looking to buy, sell, or rent a property, American Homes and Rentals LLC is here to assist you every step of the way. Contact us today to start your real estate journey!

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.

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

Framework Properties is a multifaceted institution located at 40 Railroad Street in Great Barrington, Massachusetts. As a finance company, general contractor, and real estate agency, we offer a comprehensive range of services to meet all of your property needs. Whether you are looking to invest in real estate, renovate your current property, or secure financing for a new project, our experienced team is here to help. With a focus on professionalism, integrity, and customer satisfaction, Framework Properties is your trusted partner in the world of real estate and finance.

Posto Property Management is a reputable real estate agency located at 223 Egremont Plain Road in Egremont, Massachusetts. Our dedicated team of professionals is committed to providing top-notch property management services to our clients. Whether you are looking to buy, sell, rent, or invest in real estate, we are here to assist you every step of the way. Additionally, we offer travel agency services to help you plan your next vacation or business trip with ease. Trust Posto Property Management to handle all of your real estate and travel needs efficiently and effectively.

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.

Nocher Realty is a reputable real estate agency located at 152 Main Street in Great Barrington, Massachusetts. Whether you are buying or selling a property, our experienced team is here to guide you through the process and provide you with the best possible experience. From condos to mansions, we have a wide range of properties available for you to explore. Visit us at our second location at 48 Elm Street in Pittsfield, Massachusetts for more options. Don't let the property adventure make you nervous - trust Nocher Realty to help you every step of the way.

Stone House Properties is a reputable real estate agency located at 35 Railroad Street in Great Barrington, Massachusetts, United States. With a team of experienced agents, including the highly praised Melissa Dimassimo, Stone House Properties is dedicated to providing exceptional service to clients during all stages of the real estate process. Whether you are buying, selling, or renting a property, the team at Stone House Properties is committed to making the experience as smooth and stress-free as possible. Contact Stone House Properties today for all of your real estate needs.

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.

Berkshire Property Agents is a locally-owned real estate agency located in Great Barrington, Massachusetts. Founded in 2007 by Tim Lovett and Jen Harvey, both long-time Berkshire residents, BPA serves full-time residents and second home owners in Berkshire, Columbia, and Litchfield counties. Committed to preserving the rural landscape and supporting cultural organizations in the region, BPA's team of agents maintain high professional standards and provide exceptional customer service to buyers and sellers alike. Visit us at 12 Railroad Street to experience our personalized approach to real estate.

The Verb Hotel is a stylish and retro-inspired lodging located at 1271 Boylston Street in the vibrant city of Boston, Massachusetts. This unique hotel offers a fun and funky atmosphere, with a nod to the music and pop culture of the 1960s and 70s. Guests can enjoy comfortable rooms, a lively on-site restaurant and bar, and convenient amenities such as free Wi-Fi and a fitness center. The Verb Hotel is the perfect choice for travelers looking for a one-of-a-kind experience in the heart of Boston.

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.

Benton Cove Cabins is a real estate and travel agency located at 189 Ray Hubbard Road in Otis, Massachusetts, United States. Our lakeside cabin rental, "Leeway," offers stunning sunsets and a peaceful retreat on Benton Pond. The 2024 season runs from May 17 to October 13, offering activities such as hiking, swimming, canoeing, kayaking, and more. "Leeway" comfortably sleeps six guests and features two bedrooms, a fully equipped kitchen, a bathroom with modern amenities, and a cozy living room with a stone fireplace. Guests can enjoy their private dock, gas grill, and access to row boats, a canoe, and kayaks. With 225 feet of lakefront shared with our sister cabin "Arcadia," Benton Cove Cabins is the perfect destination for families seeking a relaxing getaway in the Berkshires.

The Northampton / Springfield KOA Holiday is a picturesque campground located at 139 South Road in Westhampton, Massachusetts, United States. This charming institution offers a variety of lodging options including cabins, RV sites, and tent sites, perfect for a peaceful getaway in nature. The park features beautiful scenic views, hiking trails, a swimming pool, and recreational activities for guests of all ages. Whether you're looking for a relaxing weekend retreat or a fun-filled family vacation, the Northampton / Springfield KOA Holiday is the ideal destination for outdoor enthusiasts.

Pretty Picky Properties is a real estate and travel agency located at 2421 Main Street in Brewster, Massachusetts. Specializing in Cape Cod vacation rentals, this agency offers a wide range of properties to choose from for your next getaway. With a focus on quality and attention to detail, Pretty Picky Properties ensures that each rental meets the highest standards of comfort and convenience. Whether you're looking for a beachfront escape or a cozy cottage near hiking trails, Pretty Picky Properties has the perfect vacation rental for you. Guests rave about the beautiful homes, great locations, and superb amenities offered by this agency. The attentive owner and property management team are quick to address any issues that may arise, ensuring a stress-free stay for all guests.

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.

Island Real Estate is a prestigious real estate agency located at 107 Beach Road in Tisbury, Massachusetts. Specializing in waterfront properties and luxury homes, Island Real Estate offers a unique opportunity to own a piece of paradise on Martha's Vineyard. With panoramic views and exclusive listings like the Harthaven Waterfront Compound, this agency is the go-to destination for those seeking a dream home or vacation property. Whether you are looking to buy, sell, or rent, Island Real Estate's team of experienced agents is dedicated to helping you find the perfect property to suit your needs. Contact us today to start your journey to owning a piece of the beautiful Martha's Vineyard coastline.

The Pioneer is a reputable real estate agency located at 1760 Revere Beach Parkway in Everett, Massachusetts. With a dedicated team of experienced agents, The Pioneer is committed to helping clients find their dream homes or investment properties in the Greater Boston area. Whether you are buying, selling, or renting, The Pioneer offers personalized service and expert guidance throughout the entire real estate process. Trust The Pioneer to be your partner in achieving your real estate goals.

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.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires is a charming lodging destination nestled in the picturesque town of Lee, Massachusetts. Surrounded by the stunning beauty of the Berkshires, this resort offers a perfect retreat for families and couples looking to relax and unwind in a peaceful setting. The resort features spacious accommodations, including comfortable rooms and suites, all equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a range of on-site facilities, including indoor and outdoor pools, a fitness center, tennis courts, and a game room. There are also organized activities and events for guests of all ages to enjoy.

Beach Realty is a premier real estate and travel agency located at 133 North Shore Boulevard in Sandwich, Massachusetts. Our experienced team of agents specializes in buying and selling beachfront properties, vacation rentals, and investment properties in the beautiful coastal town of Sandwich. Whether you are looking for a dream beach house or planning a relaxing getaway, Beach Realty is here to help you find the perfect property to suit your needs. Contact us today to start your beachfront living experience!

Located at 29 Main Street in Orleans, Massachusetts, WeNeedaVacation.com is a premier institution offering lodging, real estate, and travel services. Specializing in vacation rentals on Cape Cod, Martha's Vineyard, and Nantucket since 1997, we provide a wide range of options for travelers looking to explore the beautiful beaches, natural landscapes, and unique history of these iconic destinations. From historic Plymouth to the tip of Provincetown, the Cape offers an unparalleled combination of beauty and fun activities. Martha's Vineyard Island boasts six charming towns and 110 square miles of natural beauty, while Nantucket features a preserved main town surrounded by picturesque seaside communities. We offer flexible-length plans with no hidden fees or commissions, guaranteeing booking results and providing personalized services and resources for our members. As the go-to rental site for the Cape & Islands, WeNeedaVacation.com ensures a memorable and stress-free vacation experience. For added protection, travelers can also obtain instant travel insurance quotes through our website.

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.

The Captain's House Plymouth is a charming and historic institution located at 8 Brewster Street in Plymouth, Massachusetts. As a real estate agency, they specialize in helping clients find their dream homes in this picturesque coastal town. Additionally, as a travel agency, they offer personalized vacation planning services to help visitors make the most of their time in Plymouth. With a team of experienced professionals and a deep knowledge of the local area, The Captain's House Plymouth is your go-to destination for all things real estate and travel in Plymouth, Massachusetts.

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.

Wallis Cove Cabins is a charming lodging institution nestled on Island Road in Douglas, Massachusetts, United States. Surrounded by the tranquil beauty of nature, these cozy cabins offer a peaceful retreat for guests looking to escape the hustle and bustle of everyday life. Each cabin is thoughtfully designed and equipped with modern amenities to ensure a comfortable stay. Whether you're seeking a romantic getaway or a family vacation, Wallis Cove Cabins provides the perfect setting for a memorable experience. Explore the nearby hiking trails, relax by the lake, or simply unwind on your private deck and take in the picturesque views. Experience the tranquility and serenity of Wallis Cove Cabins for a truly unforgettable stay.

Berkshire Hathaway HomeServices Barnbrook Realty is a prestigious real estate agency located in the charming town of Great Barrington, Massachusetts. Situated at 271 Main Street, this agency specializes in helping clients buy and sell residential properties in the picturesque Berkshire region. With a team of experienced and knowledgeable real estate professionals, Berkshire Hathaway HomeServices Barnbrook Realty provides top-notch service and guidance to clients looking to find their dream home or investment property. Whether you are a first-time homebuyer or a seasoned investor, this agency is dedicated to helping you navigate the real estate market with ease and confidence.

Kris Cook, Realtor with Real Broker MA LLC is a reputable real estate agency located at 147 Berkshire Drive in Westfield, Massachusetts, United States. With years of experience in the industry, Kris Cook provides top-notch service to clients looking to buy or sell property in the area. Whether you are a first-time homebuyer or a seasoned investor, Kris Cook will guide you through the process with professionalism and expertise. Contact Kris Cook, Realtor with Real Broker MA LLC today to make your real estate dreams a reality.