TOP 10 Vacation house rentals in Winchester, Massachusetts

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Barrett Sotheby's International Realty in Winchester, Massachusetts, is a prestigious real estate agency located at 48 Mount Vernon Street. With a reputation for excellence and luxury, our team of experienced agents is dedicated to helping clients buy and sell homes in the picturesque town of Winchester. Whether you are looking for a historic Victorian home or a modern luxury estate, our knowledgeable staff is here to assist you every step of the way. Trust Barrett Sotheby's International Realty to help you find your dream home in Winchester.

Welcome to David Lenoir Homes - Your Trusted Real Estate Partner in Greater Boston Located at 37 Park Avenue Extension, Arlington, Massachusetts, David Lenoir Homes is your go-to real estate agency for exploring the vibrant communities and neighborhoods of the Greater Boston Area. Whether you're a first-time homebuyer or a seasoned investor, our dedicated team is here to guide you every step of the way.

Welcome to "Making Moves in Mass - Shannon Sisk at Compass," your premier real estate agency located at 41 Thompson Street, Winchester, Massachusetts. We specialize in helping you explore and discover the best neighborhoods in Greater Boston through our intuitive and user-friendly home search platform. Our goal is to make your home buying or selling journey as seamless and stress-free as possible, with zero hassle, zero risk, and zero sacrifices. Join the countless Boston area families who have successfully leveraged our unique approach to real estate transactions. Whether you're buying or selling, we're here to ensure you achieve the best possible outcome. Ready to embark on your real estate journey? Let's get in touch today!

Welcome to Coldwell Banker Realty - Winchester, your trusted partner in navigating the real estate market in Winchester, Massachusetts, and the surrounding areas. Conveniently located at 3 Church Street, our agency is dedicated to providing exceptional service and expertise to help you achieve your real estate goals. Whether you're buying, selling, or investing, our team of experienced and knowledgeable agents is here to guide you every step of the way. We pride ourselves on our commitment to customer satisfaction, personalized service, and a deep understanding of the local market trends. Discover the difference that Coldwell Banker Realty - Winchester can make in your real estate journey. Visit us today and let us help you find your dream home or the perfect investment opportunity.

Berkshire Hathaway HomeServices Commonwealth Real Estate is a prestigious real estate agency located at 39 Church Street in Winchester, Massachusetts, United States. With a reputation for excellence and a commitment to providing top-notch service to clients, Berkshire Hathaway HomeServices Commonwealth Real Estate is a trusted name in the industry. Whether you are buying, selling, or renting a property, their team of experienced agents is dedicated to helping you achieve your real estate goals. Contact them today to experience the difference of working with a leading real estate agency.

Pierce Properties Real Estate is a reputable real estate agency located at 94 Church Street in Winchester, Massachusetts, United States. With years of experience in the industry, our team of dedicated professionals is committed to helping clients buy, sell, and rent properties in the area. Whether you're looking for your dream home or seeking to invest in real estate, we are here to guide you every step of the way. Contact us today to learn more about our services and how we can assist you in achieving your real estate goals.

Welcome to Coldwell Banker Realty - Waltham, your trusted real estate partner located at 560 Moody Street, Waltham, Massachusetts. As a premier real estate agency, we proudly serve a wide range of communities including Acton, Arlington, Ashby, Ashland, and beyond. Our dedicated team of independent contractor sales associates is committed to helping you navigate the real estate market with ease and expertise. Whether you are buying or selling a home, our comprehensive services are designed to meet your unique needs. We provide access to the latest property listings from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, ensuring you have the most current information at your fingertips. Please note that while we strive for accuracy, all properties are subject to prior sale, changes, or withdrawal.

Welcome to Coldwell Banker Realty - Lexington, your trusted real estate partner located at 1775 Massachusetts Avenue, Lexington, Massachusetts. As a premier real estate agency, we proudly serve a wide range of communities including Abington, Acton, Arlington, Ashby, Ashland, Ayer, Bedford, Belmont, Billerica, Boxborough, Burlington, Carlisle, Chelmsford, Concord, Dracut, Dunstable, Groton, Holliston, Hopkinton, Hudson, Lexington, Lincoln, Littleton, Maynard, Medford, Natick, North Reading, Pepperell, Reading, Sherborn, Shirley, Stoneham, Stow, Sudbury, Tewksbury, Townsend, Tyngsborough, Wakefield, Wayland, Westford, Weston, Wilmington, and Winchester. Our dedicated team of independent contractor sales associates is committed to providing exceptional service and personalized guidance in your real estate journey. Whether you're buying or selling, we offer comprehensive resources and expert insight to help you make informed decisions.

Welcome to the Judy Tedesco Group at Coldwell Banker Realty, your premier real estate partner located at 1775 Massachusetts Avenue, Lexington, Massachusetts. As a leading real estate agency, we are dedicated to delivering exceptional service and unparalleled expertise to our clients. Under the leadership of Judy Tedesco, a top-producing agent with 38 years of experience, we specialize in the vibrant communities of Lexington, Boston, Winchester, Concord, Arlington, Wellesley, and surrounding towns. We are thrilled to announce our new chapter with Coldwell Banker Realty, the #1 brokerage in Lexington. This strategic move empowers us to offer exclusive listing resources and unique access to both on- and off-market properties, ensuring our clients receive the highest level of support and opportunities in the real estate market.

Welcome to Lorie Glantz & Sandy Saia, Realtors at Coldwell Banker Realty in Burlington, Massachusetts. Conveniently located at 202 Cambridge Street, we are your trusted partners in navigating the dynamic real estate market of Middlesex County and the greater Boston suburbs. Whether you're searching for your dream home or looking to sell your property, our dedicated team is here to provide you with exceptional service and expert guidance. Our website offers the freshest data available, featuring active listings only. With customizable search options and new listing alerts, you can stay ahead in the competitive real estate market. Instantly assess home values and explore the newest real estate listings in the area, ensuring you never miss an opportunity.

Welcome to Top Home Team, your premier real estate agency located at 202 Cambridge Street, Burlington, Massachusetts. Specializing in the vibrant and diverse Middlesex County, we are committed to providing you with the freshest and most comprehensive real estate listings available. Whether you're searching for a charming home or a modern condo in the Boston suburbs, our team is dedicated to helping you find the perfect property. At Top Home Team, we pride ourselves on offering active listings only, ensuring you have access to the latest properties on the market. Our customizable search options and new listing alerts make it easy for you to stay ahead of the curve. Plus, with our instant home value assessments, you can make informed decisions with confidence.

Welcome to Brenda Cahoon REALTOR - EXIT Premier Real Estate, your trusted partner in Burlington, Massachusetts, for all your real estate needs. Conveniently located at 85 Wilmington Road, our office is dedicated to providing exceptional service and personalized attention to each of our clients. Whether you're buying, selling, or investing in property, Brenda Cahoon and her team are committed to guiding you through every step of the process with expertise and integrity. With a deep understanding of the local market and a passion for helping clients achieve their real estate goals, we strive to make your experience seamless and rewarding. Visit us today and discover how Brenda Cahoon REALTOR - EXIT Premier Real Estate can turn your property dreams into reality.

Welcome to Coldwell Banker Realty - Newton, your trusted real estate agency located at 1261 Centre Street, Newton, Massachusetts. As a leading agency in the region, we proudly serve a wide array of communities including Acton, Arlington, Belmont, Brookline, Lexington, Newton, Wellesley, and many more. Our team of dedicated real estate professionals is committed to providing exceptional service to both home sellers and buyers, ensuring a seamless and rewarding experience. Under the leadership of our Vice President and Managing Broker, our Newton and Chestnut Hill offices have thrived, thanks to a vibrant office environment and a commitment to continuous agent training. Our sales associates are equipped with innovative tools, resources, and exceptional marketing strategies to help you achieve your real estate goals.

Welcome to BrokerKing Realty, your trusted real estate agency located at 27 Bennett Road, Watertown, Massachusetts. At BrokerKing Realty, we are committed to providing exceptional real estate services in the Watertown area and beyond. Led by Mr. Alexander Kupelian, our team is dedicated to helping you navigate the complexities of buying and selling properties with ease and confidence. Mr. Kupelian is renowned for his excellence in the real estate business, consistently going above and beyond to ensure client satisfaction. Whether you're looking to sell your home or purchase a new one, you can count on his professionalism, punctuality, and honesty. He is known for his hard work and reliability, always striving to accommodate and satisfy his clients' unique needs.

Welcome to The Abundant Group, your premier real estate agency located at 45 Amberwood Drive, Winchester, Massachusetts. Specializing in a comprehensive range of real estate services, we offer the best search tools for homes, condos, rentals, land, and foreclosure properties in the area. Our user-friendly website is your ultimate resource, updated every 15 minutes directly from the official Realtor® database to ensure you receive the most current listings. At The Abundant Group, we provide innovative features to enhance your property search experience. Save your favorite searches and receive daily email alerts about new listings, price changes, and market trends. Explore our Interactive Map Search to view properties in your desired area or draw custom boundaries to refine your search. Stay informed about your neighborhood's real estate market with personalized market reports that detail active, under contract, and sold properties.

Welcome to Lawton Real Estate, Inc Located at 4 Bennett Street, Woburn, Massachusetts, Lawton Real Estate is your trusted local partner in the real estate market. As a small, fiercely independent agency, we pride ourselves on offering personalized and dedicated service to each of our clients. Whether you're just starting your real estate journey and conducting research, or you know precisely what you're looking for, our team of experienced professionals is here to guide you every step of the way.

Welcome to LivNJoy PBC, Inc., your trusted real estate partner located in the heart of Winchester, Massachusetts. Situated at 29 Dunster Lane, we specialize in providing exceptional real estate services tailored to meet the unique needs of our clients. Whether you're buying, selling, or investing in properties, our team of experienced professionals is dedicated to guiding you through every step of the process with integrity and expertise. At LivNJoy PBC, Inc., we pride ourselves on our deep knowledge of the local market and our commitment to delivering personalized solutions that help you achieve your real estate goals. Discover a seamless and rewarding real estate experience with us today!

Welcome to Greater Metropolitan Real Estate, your premier real estate agency located in the heart of Winchester, Massachusetts. Situated at 872 Main Street, we pride ourselves on delivering exceptional service to our clients across the Greater Boston area. Our team of experienced and dedicated professionals is committed to guiding you through every step of your real estate journey, whether you're buying, selling, or investing in property. At Greater Metropolitan Real Estate, we understand that each client's needs are unique. That's why we offer personalized solutions tailored to your specific goals. With an in-depth knowledge of the local market and a passion for real estate, we provide expert advice and insights to help you make informed decisions. Our comprehensive services include property listings, market analysis, and negotiation expertise, ensuring a seamless and stress-free experience.

Welcome to The Marino Group Collection, your premier real estate agency located in the heart of Winchester, Massachusetts. Situated at 842 Main Street, we specialize in providing personalized and professional real estate services tailored to meet the unique needs of our clients. Whether you're buying, selling, or investing in property, our knowledgeable team is dedicated to guiding you through every step of the process with expertise and care. At The Marino Group Collection, we pride ourselves on our deep understanding of the local market, commitment to customer satisfaction, and a proven track record of successful transactions. Discover the difference of working with a trusted partner in real estate. Visit us today and let us help you find your dream home or the perfect investment opportunity in Winchester and beyond.

Welcome to The Elle Group, your trusted real estate partner located in the heart of Winchester, Massachusetts. Situated at 39 Church Street, Winchester, MA 01890, our agency is dedicated to providing exceptional real estate services to individuals and families looking to buy, sell, or rent properties in the area. At The Elle Group, we pride ourselves on our deep understanding of the local market, our commitment to client satisfaction, and our ability to tailor our services to meet your unique needs. Our team of experienced and knowledgeable real estate professionals is here to guide you through every step of the process, ensuring a seamless and stress-free experience.

Welcome to Kim Covino & Co., your trusted real estate partner located at 41 Thompson Street, Winchester, Massachusetts. As a premier real estate agency, we are dedicated to providing exceptional service to both sellers and buyers in Winchester and beyond. With over 30 years of experience, Kim Covino & Co. is consistently ranked among the top-tier brokers in the community, offering unparalleled expertise and a personalized approach to every client. For sellers, we ensure your home's presentation is impeccable by utilizing our exclusive suite of contractor services, which includes customized staging and award-winning photography. Our proven track record in negotiating and sourcing buyers from various markets is bolstered by our premiere listings and a strong referral base, ensuring your property receives the attention it deserves.

Welcome to Gayle Winters & Co - Compass, your trusted real estate agency located in the heart of Winchester, Massachusetts. Situated at 41 Thompson Street, our team is dedicated to providing exceptional real estate services to the Winchester community and beyond. With a deep understanding of the local market and a commitment to personalized service, we are here to guide you through every step of your real estate journey. Whether you are buying, selling, or investing, Gayle Winters & Co - Compass offers expert advice and innovative solutions tailored to your unique needs. Our experienced agents are passionate about helping you find the perfect home or achieve the best value for your property. We pride ourselves on our integrity, professionalism, and dedication to making your real estate experience seamless and rewarding.

Welcome to Katherine Waters-Clark COMPASS, your premier real estate agency located in the heart of Winchester, Massachusetts. Situated at 41 Thompson Street, our agency is dedicated to providing exceptional real estate services to the Winchester community and surrounding areas. With a deep understanding of the local market, Katherine Waters-Clark COMPASS is committed to helping you navigate the complexities of buying or selling your home with ease and confidence. Our team of experienced real estate professionals is passionate about delivering personalized service tailored to meet your unique needs. Whether you're a first-time homebuyer, looking to upgrade, or seeking investment opportunities, we offer expert guidance and support every step of the way.

Welcome to The McLaren Team, your trusted real estate agency located at 48 Mount Vernon Street, Winchester, Massachusetts. With over 50 years of combined experience and a decade as a dedicated team, we are committed to guiding you through every step of your real estate journey, whether you are buying your dream home or selling your current property. Our mission is to align our goals with yours, ensuring that you make a sound investment decision and find a place to truly call home. Our team stands out with diverse expertise in finance, luxury marketing, and new construction development, allowing us to provide comprehensive service and unparalleled market insight. We pride ourselves on making the process as seamless as possible, offering personalized support from the initial stages to long after the closing.

Welcome to Julie Wile Fish Real Estate - Leading Edge Real Estate, your premier real estate agency located in the heart of Winchester, Massachusetts. Situated at 2 Mount Vernon Street, our agency is dedicated to providing exceptional real estate services to the local community and beyond. With a passion for helping clients find their dream homes or sell their properties at optimal value, our team of experienced professionals is committed to delivering personalized, results-driven service. At Julie Wile Fish Real Estate, we understand that buying or selling a home is more than just a transaction; it's a life-changing experience. That's why our team is devoted to guiding you through every step of the process with expertise, integrity, and unparalleled market knowledge. Whether you are a first-time homebuyer, looking to upgrade, or interested in investment properties, we tailor our approach to meet your unique needs and goals.

Welcome to Conforti & Medina Realtors, your trusted partner in real estate and general contracting services, located at 3 Church Street, Winchester, Massachusetts. With a steadfast commitment to excellence and customer satisfaction, we specialize in helping you find your dream home and transform properties to meet your unique needs. Our experienced team of real estate professionals is dedicated to providing personalized service, whether you're buying, selling, or investing in property. As a full-service general contractor, we also offer comprehensive renovation and construction solutions to enhance the value and functionality of your space. At Conforti & Medina Realtors, we pride ourselves on our deep local knowledge and a network of resources to ensure a seamless and rewarding experience for our clients. Visit us today to explore how we can assist you on your real estate journey.

Welcome to Andersen Group Realty - Keller Williams Realty Boston NW, your trusted partner in navigating the real estate landscape of Winchester and the greater Boston area. Located at 17 Waterfield Road, Winchester, Massachusetts, our agency is dedicated to providing exceptional service to buyers, sellers, and investors alike. With a deep understanding of the local market and a commitment to excellence, our team of experienced professionals is here to guide you through every step of your real estate journey. Whether you're looking to find your dream home, sell a property, or explore investment opportunities, Andersen Group Realty combines local expertise with the global resources of Keller Williams Realty to deliver results that exceed your expectations. Visit us today and experience the difference of working with a team that truly cares about your real estate goals.

Welcome to Leading Edge Real Estate, your trusted partner in navigating the dynamic real estate market of Winchester, Massachusetts, and beyond. Conveniently located at 2 Mount Vernon Street, our agency is dedicated to providing exceptional service and expert guidance to both buyers and sellers. At Leading Edge Real Estate, we pride ourselves on our deep local knowledge and commitment to our clients' success. Our experienced team of real estate professionals is passionate about helping you find your dream home or achieve the best possible outcome for your property sale. Whether you're a first-time homebuyer, looking to upgrade, or interested in investment opportunities, we tailor our approach to meet your unique needs and goals.

Welcome to Jay Noble Real Estate - Compass, your trusted partner in navigating the Winchester, Massachusetts real estate market. Conveniently located at 41 Thompson Street, our agency is dedicated to providing exceptional service and expert guidance to help you find your dream home or sell your property with ease. With a deep understanding of the local market and a commitment to personalized service, Jay Noble Real Estate - Compass offers a comprehensive suite of real estate solutions tailored to meet your unique needs. Whether you are a first-time homebuyer, looking to upgrade, or interested in investment properties, our experienced team is here to support you every step of the way.

Welcome to Better Homes and Gardens Real Estate The Shanahan Group, your trusted local real estate partner located at 552 Main Street, Winchester, Massachusetts. Our agency is dedicated to providing exceptional real estate services to the vibrant communities of Winchester and the surrounding areas. With a deep understanding of the local market and a commitment to personalized service, we guide our clients through every step of the buying, selling, or renting process. Whether you're a first-time homebuyer, a seasoned investor, or looking to sell your property, our experienced team is here to help you achieve your real estate goals with ease and confidence. Discover the difference of working with a team that combines local expertise with the trusted national brand of Better Homes and Gardens Real Estate. Visit us today and let us turn your real estate dreams into reality.