TOP 30 Vacation house rentals in Great Barrington, Massachusetts

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Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.

Welcome to Quality Inn Great Barrington, a 100% smoke-free hotel located at 372 Main Street in the charming forested mountain town of Great Barrington, Massachusetts. Whether you are visiting for business or pleasure, our hotel offers excellent value and a range of amenities to ensure a great experience during your stay. Our hotel features free wifi throughout the property, a complimentary continental breakfast each morning, free parking, an exercise room, and 24-hour desk service. Each room is equipped with a fridge, microwave, flat-screen television, desk with chair, coffee maker, and more. We strive to provide all the amenities you expect, along with special touches to enhance your Berkshires experience.

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

The Barrington Bed and Breakfast is a charming lodging establishment located at 281 Main Street in the picturesque town of Great Barrington, Massachusetts. This cozy B&B offers a warm and inviting atmosphere for guests looking for a relaxing getaway in the heart of the Berkshires. The beautifully decorated rooms are equipped with modern amenities to ensure a comfortable stay, and guests can enjoy a delicious homemade breakfast each morning. Conveniently located near shops, restaurants, and attractions, The Barrington Bed and Breakfast is the perfect choice for those seeking a peaceful retreat in a quaint New England town.

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.

Econo Lodge Lee - Great Barrington is a cozy and affordable lodging option located at 980 Pleasant Street in Lee, Massachusetts, United States. Situated in a convenient location, this institution offers comfortable accommodations and a range of amenities for guests to enjoy during their stay. Whether you are traveling for business or leisure, Econo Lodge Lee - Great Barrington provides a welcoming atmosphere and friendly service to ensure a pleasant experience for all guests.

Welcome to William Pitt Sotheby's International Realty - Great Barrington Brokerage, your premier destination for exceptional real estate services in the heart of the Berkshires. Located at 306 Main Street, Great Barrington, Massachusetts, our office blends the prestige of a world-renowned real estate brand with the warmth and expertise of local market knowledge. Our team is committed to providing sophisticated yet personable service to our discerning clients, ensuring a seamless experience whether you're buying or selling a home. The Berkshires, a stunning year-round resort destination, is known for its picturesque landscapes, vibrant cultural scene, and a lifestyle that combines relaxation with refinement. This area attracts a diverse array of residents from around the globe, drawn by its creative energy, world-class artisans, and exceptional farm-to-table dining experiences.

Welcome to Anna Fernandez-Gevaert - Best Second Home Realtor in the Berkshires, located at 271 Main Street, Great Barrington, Massachusetts. As a premier real estate expert in the scenic Berkshires region, Anna Fernandez-Gevaert is dedicated to helping you find the perfect second home that suits your lifestyle and needs. With an in-depth knowledge of the local market and a passion for personalized service, Anna provides unparalleled guidance through every step of the buying process. Whether you're seeking a tranquil retreat amidst nature or a charming property in a vibrant community, Anna's expertise and commitment ensure a seamless and rewarding experience. Discover your dream second home in the Berkshires with the trusted assistance of Anna Fernandez-Gevaert. Visit us today and take the first step towards your perfect getaway.

The Inn at Freeman Elms Farm B&B is a charming and welcoming lodging establishment located in the picturesque town of New Marlborough, Massachusetts. Situated at 566 Mill River Great Barrington Road, this historic bed and breakfast offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by the natural beauty of the Berkshires, the Inn at Freeman Elms Farm B&B provides a cozy and comfortable atmosphere for guests to unwind and recharge. The property boasts beautifully appointed rooms, each uniquely decorated to provide a home away from home experience. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients.

Welcome to Monument Mountain Motel, a budget-friendly lodging option in the heart of Great Barrington, Massachusetts. Located in the beautiful Berkshire Mountains, our motel offers comfortable rooms and family-style amenities. Whether you're in town for business or pleasure, our convenient location puts you near iconic attractions such as Tanglewood Music Festival, Ski Butternut Resort, and the Norman Rockwell Museum. At Monument Mountain Motel, we strive to provide a pleasant and affordable experience for all our guests. Enjoy free wifi, in-room microwaves and fridges, and a spacious patio with barbecue facilities. Family travelers will appreciate our family-friendly amenities, while business travelers will find our simplicity and affordability to be just what they need.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

Lantern House Motel is a charming lodging establishment located at 256 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts, United States. Offering comfortable and affordable accommodations, this quaint motel is the perfect choice for travelers looking to explore the beautiful Berkshires region. With its convenient location and friendly staff, Lantern House Motel provides a cozy home away from home for guests looking to relax and unwind during their stay. Whether you are visiting for business or pleasure, you are sure to enjoy your time at this welcoming institution.

Briarcliff Motel is a charming lodging establishment located at 506 Stockbridge Road in Great Barrington, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beauty of the region. With its convenient location and friendly staff, Briarcliff Motel is the perfect choice for a relaxing getaway in the heart of New England.

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.

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.

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.

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.

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.

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.

Helen Mullany Real Estate is a reputable real estate agency located at 183 Main Street in Great Barrington, Massachusetts. With a team of experienced and knowledgeable real estate agents, they specialize in helping clients buy and sell residential and commercial properties in the area. Whether you are looking for your dream home or trying to sell your current property, Helen Mullany Real Estate is committed to providing top-notch service and guidance throughout the entire process. Contact them today to learn more about their services and how they can assist you with your real estate needs.

Jessie Bennett is a renowned Berkshire Real Estate Expert located at 271 Main Street in Great Barrington, Massachusetts. With years of experience and a deep understanding of the local market, Jessie Bennett is dedicated to helping clients buy, sell, or invest in properties in the Berkshire area. Whether you are looking for a luxury estate, a charming cottage, or a commercial property, Jessie Bennett has the expertise and resources to guide you through the real estate process with professionalism and care. Trust Jessie Bennett to be your partner in achieving your real estate goals in the beautiful Berkshire region.

Welcome to Berkshire Property Care, your trusted real estate partner in the heart of the Berkshires. Conveniently located at 21 Hemlock Hill Road, Great Barrington, Massachusetts, our agency specializes in providing exceptional real estate services tailored to meet your unique needs. Whether you're buying, selling, or investing in property, our team of experienced professionals is dedicated to guiding you every step of the way. We pride ourselves on our deep local knowledge, personalized service, and commitment to excellence, ensuring a seamless and rewarding experience for all our clients. Discover the Berkshire difference and let us help you find your perfect property today.

Welcome to Lance Vermeulen Real Estate, Inc., your trusted partner in real estate located in the heart of Great Barrington, Massachusetts. Situated at 283 Main Street, we are proud to serve the vibrant communities of the Berkshires with unparalleled expertise and personalized service. Our dedicated team of real estate professionals is committed to helping you navigate the dynamic property market, whether you're buying, selling, or renting. With a deep understanding of the local landscape and a passion for matching clients with their perfect homes, we strive to make your real estate journey seamless and rewarding. Visit us today to discover how we can assist you in achieving your real estate goals. Experience the difference with Lance Vermeulen Real Estate, Inc., where your satisfaction is our priority.

Welcome to Jen Harvey, BERKSHIRE PROPERTY AGENTS, LLC, your trusted partner in real estate located in the heart of Great Barrington, Massachusetts. Situated at 12 Railroad Street, our agency specializes in providing exceptional real estate services throughout the picturesque Berkshire region. Whether you're looking to buy, sell, or rent a property, our dedicated team is committed to guiding you through every step of the process with personalized attention and expert advice. With an in-depth knowledge of the local market and a passion for the community, we strive to make your real estate experience seamless and rewarding. Discover the difference with Jen Harvey, BERKSHIRE PROPERTY AGENTS, LLC, where your property dreams become a reality. Visit us today to explore the best of what the Berkshires have to offer.