TOP 10 Vacation house rentals in Sag Harbor, New York

Welcome to Brown Harris Stevens of Sag Harbor, your premier real estate agency located in the heart of the historic village at 96 Main Street, Sag Harbor, New York. Nestled in the picturesque Hamptons, our office is dedicated to providing exceptional real estate services tailored to meet the unique needs of our clients. With a rich history of excellence and a deep understanding of the local market, our team of experienced professionals is committed to helping you find your dream home or the perfect investment property. Whether you're buying, selling, or renting, we offer personalized guidance and unparalleled expertise to ensure a seamless and rewarding real estate experience. Discover the charm of Sag Harbor and the beauty of the surrounding areas with Brown Harris Stevens, where your real estate goals are our top priority. Visit us today and let us be your trusted partner in navigating the Hamptons real estate landscape.

Welcome to Douglas Elliman Real Estate Office in Sag Harbor, NY, your premier destination for all your real estate needs. Conveniently located at 138 Main Street in the heart of the charming village of Sag Harbor, our office is dedicated to providing exceptional real estate services in this picturesque corner of the Hamptons. At Douglas Elliman Sag Harbor, we pride ourselves on our deep local knowledge and our commitment to delivering personalized service to each of our clients. Whether you are looking to buy, sell, or rent a property, our team of experienced real estate professionals is here to guide you every step of the way. We specialize in a wide range of properties, from luxurious waterfront estates to cozy village homes, ensuring we have the perfect fit for every lifestyle and budget.

Welcome to Cynthia Barrett - Real Estate Agent, your premier Hamptons residential realtor located in the heart of Bridgehampton. Situated at 2408 Main Street, Bridgehampton, NY, Cynthia Barrett specializes in providing personalized real estate services throughout the stunning locales of Bridgehampton, Sag Harbor, and Shelter Island. With years of experience and an unparalleled understanding of the Hamptons' unique market, Cynthia is dedicated to helping you find your dream home or the perfect buyer for your property. Whether you are seeking a serene summer retreat, a vibrant year-round residence, or an investment opportunity, Cynthia's expertise and commitment ensure a seamless and rewarding real estate experience.

Welcome to Sag Harbor Inn, your quintessential retreat nestled in the heart of the historic and picturesque Sag Harbor, New York. Located at 45 West Water Street, our charming inn offers a perfect blend of comfort, style, and tranquility, making it an ideal destination for both leisure and business travelers. At Sag Harbor Inn, we pride ourselves on providing exceptional hospitality and personalized service. Our beautifully appointed rooms offer breathtaking views of the harbor and are designed to ensure a relaxing and memorable stay. Each room features modern amenities, including complimentary Wi-Fi, flat-screen TVs, and plush bedding, to cater to your every need.

Sunset Beach Hotel is a charming and picturesque institution located at 35 Shore Road in Shelter Island Heights, New York. This multifaceted establishment offers a variety of services including a clothing store, food, lodging, and a restaurant. The boutique hotel features beautifully designed rooms with stunning views of the surrounding area. Guests can also enjoy delicious meals and refreshing drinks at the on-site restaurant and bar. Ferry service to Shelter Island is available from both the North Fork of Long Island via Greenport and the South Fork via Sag Harbor, making it easily accessible for visitors. Please note that reservations are not accepted and traffic is boarded on a first come, first serve basis. Vehicles and bicycles can pay on board with cash only. The operating schedule is limited until June 22nd, with service available on Fridays, Saturdays, Sundays, and major holidays. Be sure to check with the Ferry Companies for schedules and fares. Visit Sunset Beach Hotel for a relaxing and enjoyable experience on Shelter Island.

Welcome to The American Hotel, a historic gem nestled in the heart of Sag Harbor, New York. Located at 45 Main Street, our exquisite establishment offers a unique blend of timeless elegance and modern comfort, making it the perfect destination for both dining and lodging. At The American Hotel, we pride ourselves on providing an unforgettable culinary experience. Our renowned restaurant features a menu crafted with the finest local ingredients, offering a delightful array of dishes that celebrate the rich flavors of American cuisine. Whether you're enjoying a casual lunch or an intimate dinner, our attentive staff ensures a dining experience that is both memorable and satisfying.

Welcome to Baron's Cove, your ultimate destination for relaxation and entertainment in the heart of Sag Harbor, New York. Nestled at 31 West Water Street, our unique establishment offers an unparalleled blend of comfort, style, and vibrant nightlife, making it the perfect getaway for both locals and visitors alike. At Baron's Cove, we pride ourselves on providing a seamless experience that caters to all your needs. Our charming lodging options offer a cozy retreat with stunning views and top-notch amenities, ensuring a restful stay. Whether you're here for a weekend escape or an extended vacation, our attentive staff is dedicated to making your visit unforgettable.

Welcome to Topping Rose House, a luxurious retreat nestled in the heart of Bridgehampton, New York. Located at 1 Bridgehampton-Sag Harbor Turnpike, our historic property offers an unparalleled lodging experience in the scenic Hamptons. As a full-service hotel, Topping Rose House combines timeless elegance with modern sophistication. Our beautifully appointed rooms and suites are designed to provide the utmost comfort and relaxation. Guests can indulge in our on-site amenities, including a world-class restaurant showcasing farm-to-table cuisine, a rejuvenating spa, and a state-of-the-art fitness center.

Welcome to Prudential, your trusted real estate agency located in the charming village of Sag Harbor, New York. Nestled in the heart of the Hamptons, we specialize in providing personalized and professional real estate services tailored to meet the unique needs of our clients. Whether you're looking to buy, sell, or rent a property, our team of experienced agents is committed to guiding you through every step of the process with integrity and expertise. At Prudential, we pride ourselves on our deep local knowledge and strong community connections, ensuring you have access to the finest properties in Sag Harbor and the surrounding areas. From quaint historic homes to luxurious waterfront estates, we offer a diverse portfolio to suit every lifestyle and budget.

Welcome to Mala Sander Team at The Corcoran Group, your premier real estate agency specializing in the luxurious Hamptons market. Conveniently located at 35 Main Street, Sag Harbor, New York, we are dedicated to representing and selling the finest properties across the Hamptons, including Southampton, Sag Harbor, Water Mill, Bridgehampton, Sagaponack, Wainscott, and East Hampton. With over 20 years of experience, Mala Sander is a leading expert in the Hamptons real estate scene, consistently ranking among the top agents nationwide. Her commitment to understanding the unique lifestyles of her clients has earned her a loyal following, from local business owners to international elites. Mala's strategic, client-focused approach ensures every transaction is tailored to meet your specific needs, offering insightful market analysis and guidance.

Welcome to Patrick McLaughlin - Realtor, your trusted real estate partner located in the heart of Sag Harbor, New York. Nestled at 138 Main Street, our agency is dedicated to providing exceptional service to both buyers and sellers in the vibrant Hamptons real estate market. With a keen understanding of the local area and a commitment to personalized service, Patrick McLaughlin and his team offer expert guidance in finding your dream home or securing the best deal for your property. Whether you're looking for a charming coastal cottage, a luxurious waterfront estate, or an investment opportunity, we are here to help every step of the way. Discover the difference with Patrick McLaughlin - Realtor, where your real estate goals become our top priority. Visit us today or contact us to begin your journey in Sag Harbor’s thriving real estate market.

Welcome to The Corcoran Group, your premier real estate agency located in the heart of Sag Harbor at 35 Main Street, New York. With a longstanding reputation for excellence, we specialize in connecting clients with their dream homes and investment properties throughout the picturesque Hamptons region. Our team of experienced and dedicated real estate professionals is committed to providing personalized service, whether you're buying, selling, or renting. At The Corcoran Group, we understand the unique charm and allure of Sag Harbor and its surrounding areas, and we leverage our local expertise to ensure a seamless and rewarding real estate experience. Discover the perfect property with us today and let us help you turn your real estate dreams into reality.

Welcome to Dennis Saglam, Douglas Elliman Real Estate, your premier destination for exceptional real estate services in Sag Harbor, New York. Nestled in the heart of this charming and historic village at 138 Main Street, our office is dedicated to providing unparalleled expertise and personalized service to both buyers and sellers. At Dennis Saglam, we understand that real estate is more than just a transaction—it's about finding the perfect home or investment that aligns with your lifestyle and goals. Our team of experienced professionals is deeply rooted in the local community and possesses an in-depth knowledge of the Hamptons real estate market. We pride ourselves on our commitment to excellence, integrity, and customer satisfaction.

Welcome to Simon The Broker, your trusted partner in real estate located at 6 Long Wharf, Sag Harbor, New York. As a premier real estate agency, we specialize in navigating the luxury market in The Hamptons, offering deep insights and unparalleled expertise to both buyers and sellers. Our offerings include exquisite properties such as a 4-bedroom, 3-bath home featuring a spacious 2000 sq. ft. layout and a 16x32 pool, and a stunning 2-bedroom, 2-bath waterfront property spanning 1200 sq. ft. We're committed to staying ahead of industry trends through innovative strategies and a deep understanding of the local market.

Welcome to Simon Harrison Real Estate, your trusted partner in navigating the dynamic real estate market of The Hamptons. Located at 1 Bay Street, Sag Harbor, New York, our agency is dedicated to providing exceptional service and expert guidance to both buyers and sellers. At Simon Harrison Real Estate, we specialize in luxury properties, offering a diverse portfolio that includes stunning waterfront homes and spacious family residences. Whether you're interested in a 4-bedroom, 3-bathroom property with a 16x32 pool or a charming 2-bedroom, 2-bathroom waterfront retreat, we have the expertise to help you find your dream home.

Welcome to Sotheby's International Realty, your premier real estate agency located in the heart of Sag Harbor, New York. Situated at 35 Main Street, our office is perfectly positioned to serve the vibrant communities of the Hamptons and beyond. As a distinguished name in luxury real estate, we specialize in connecting discerning buyers and sellers with exquisite properties that match their unique lifestyles and preferences. Our team of experienced and dedicated real estate professionals is committed to delivering unparalleled service, leveraging our global network and local expertise to provide exceptional guidance at every step of your real estate journey. Whether you're looking to buy a charming coastal retreat, sell a prestigious estate, or invest in a lucrative property, Sotheby's International Realty offers a personalized approach tailored to your individual needs.

Welcome to Lorraine Pharaoh Brandon, Douglas Elliman Real Estate, your trusted partner in navigating the vibrant real estate market of Sag Harbor and the surrounding areas. Conveniently located at 138 Main Street, Sag Harbor, New York, our office is at the heart of this historic and picturesque village, renowned for its charming streets, stunning waterfronts, and rich cultural heritage. With years of experience and a deep understanding of the local market, Lorraine Pharaoh Brandon is dedicated to providing personalized and professional service to every client. Whether you are buying, selling, or renting, our team is committed to helping you achieve your real estate goals with ease and confidence.

Welcome to Team Michael Daly, your premier real estate partner located at 138 Main Street, Sag Harbor, New York. Nestled in the heart of the charming and historic village of Sag Harbor, we specialize in providing exceptional real estate services tailored to meet the unique needs of our clients. Whether you're buying, selling, or renting, our dedicated team of experienced professionals is committed to delivering personalized, attentive service to ensure a seamless and rewarding experience. At Team Michael Daly, we pride ourselves on our deep community roots and extensive knowledge of the local market. Our passion for Sag Harbor and the surrounding areas drives us to help you find the perfect home or investment property that aligns with your lifestyle and goals. We understand that real estate is more than just a transaction—it's about building relationships and helping you achieve your dreams.

Welcome to Helen Gifford Real Estate, your trusted partner in finding the perfect home or investment property in the heart of Sag Harbor, New York. Conveniently located at 35 Main Street, our agency prides itself on offering personalized, professional, and reliable real estate services to both buyers and sellers. With a deep understanding of the local market and a commitment to excellence, our team is dedicated to helping you navigate the complexities of real estate transactions with ease. Whether you're searching for a charming coastal retreat, a modern family home, or a lucrative investment opportunity, Helen Gifford Real Estate is here to guide you every step of the way. Discover the unique charm and vibrant community of Sag Harbor with us, and let us turn your real estate dreams into reality. Visit us today and experience the difference of working with a local expert who truly cares.

Welcome to Compass Real Estate, your trusted partner in navigating the vibrant real estate market of Sag Harbor, New York. Conveniently located at 84 Main Street, Compass Real Estate is dedicated to providing exceptional service and expertise to help you achieve your real estate goals. As a premier real estate agency, we specialize in connecting buyers and sellers with their ideal properties, offering personalized guidance every step of the way. Our unique Concierge service is designed to help you sell your home faster and for a higher price by covering the cost of essential home improvement services. With no upfront fees, payment is only required upon closing, making the process seamless and stress-free.

Welcome to Kelly Nelson Real Estate Agency, your trusted partner in finding the perfect home or investment property in the charming village of Sag Harbor, New York. Conveniently located at 35 Main Street, our agency is dedicated to providing exceptional service and expert guidance in the vibrant and competitive real estate market of the Hamptons. At Kelly Nelson, we understand that buying or selling a property is more than just a transaction; it's a life-changing experience. That's why our team of experienced real estate professionals is committed to delivering personalized solutions tailored to meet your unique needs and preferences. Whether you're searching for a cozy waterfront cottage, a luxurious estate, or a promising commercial property, we have the local expertise and market knowledge to help you make informed decisions.

Welcome to Robert Florio Real Estate, your trusted partner in finding the perfect home or investment property in the heart of Sag Harbor, New York. Conveniently located at 35 Main Street, our agency is dedicated to providing exceptional real estate services to both buyers and sellers in this picturesque and historic community. At Robert Florio Real Estate, we understand that buying or selling a property is more than just a transaction; it’s a life-changing experience. That’s why our team of experienced and knowledgeable agents is committed to delivering personalized, professional, and attentive service tailored to your unique needs. Whether you're searching for a charming waterfront home, a cozy cottage, or a lucrative investment opportunity, we are here to guide you every step of the way.

Welcome to Gioia DiPaolo, Licensed Associate Broker at Douglas Elliman Real Estate, your trusted partner in navigating the vibrant real estate market of Sag Harbor, New York. Located at 138 Main Street, Gioia offers unparalleled expertise and personalized service to help you find your dream home or sell your property with confidence. With a deep understanding of the local community and real estate trends, Gioia is committed to delivering exceptional results tailored to meet your unique needs. Whether you're a first-time homebuyer, seasoned investor, or looking to relocate, Gioia DiPaolo provides insightful guidance and professional support every step of the way. Discover the charm of Sag Harbor and explore the finest properties with a broker who truly understands your aspirations. Contact Gioia today to make your real estate dreams a reality.

Welcome to Susan Sprott Real Estate, your trusted partner in finding the perfect home or investment property in the heart of Sag Harbor, New York. Conveniently located at 35 Main Street, our agency is dedicated to providing personalized and professional real estate services to both buyers and sellers in the Hamptons area. With a deep understanding of the local market and a commitment to excellence, our team is here to guide you through every step of the real estate process. Whether you're searching for a charming waterfront home, a cozy cottage, or a lucrative investment opportunity, we are here to make your real estate dreams a reality. Visit us today and experience the difference of working with a team that truly cares about your needs and aspirations.

Welcome to Richard Kudlak Licensed Real Estate Salesperson at Douglas Elliman, your trusted partner in navigating the vibrant real estate market of Sag Harbor and the surrounding areas. Located at 138 Main Street, Sag Harbor, New York, our office is at the heart of this charming and historic village, known for its picturesque beauty and rich maritime heritage. Richard Kudlak brings a wealth of experience and a personalized approach to real estate, ensuring that each client receives exceptional service tailored to their unique needs. Whether you are buying, selling, or renting, Richard is committed to providing insightful guidance and expert advice to help you make informed decisions.

Welcome to George Heine Realty, your trusted partner in real estate located in the picturesque Sag Harbor, New York. Situated at 3495 Noyack Road, our agency is dedicated to providing exceptional real estate services to the vibrant communities of the Hamptons and beyond. With years of experience and a deep understanding of the local market, our team is committed to helping you find your dream home, perfect investment property, or ideal rental. At George Heine Realty, we pride ourselves on our personalized approach, ensuring that each client receives the attention and expertise they deserve. Whether you are buying, selling, or renting, our knowledgeable agents are here to guide you every step of the way. We specialize in a wide range of properties, from charming cottages and luxurious waterfront estates to commercial spaces and land opportunities.

Welcome to Berkshire Hathaway Laffey International Realty - Hamptons, your premier destination for luxury real estate services in Sag Harbor and the surrounding Hamptons area. Conveniently located at 3330 Noyack Road, Sag Harbor, New York, our office is dedicated to providing unparalleled expertise and personalized service for all your real estate needs. Whether you are buying, selling, or investing in property, our team of experienced professionals is committed to guiding you through every step of the process. We specialize in a wide range of properties, from stunning waterfront estates to charming vacation homes, ensuring that you find the perfect match for your lifestyle and preferences.

Welcome to East End Listings, your premier real estate agency located in the heart of Sag Harbor, New York. Situated at 4098 Noyack Road, our agency specializes in helping you find your dream home or perfect investment property in the beautiful East End of Long Island. With a deep understanding of the local market, our dedicated team of experienced realtors is committed to providing personalized service and expert guidance every step of the way. Whether you're buying, selling, or renting, East End Listings offers a comprehensive range of services tailored to meet your unique needs. Explore the charm of the Hamptons with us and discover why so many choose East End Listings as their trusted real estate partner. Visit us today and let us help you turn your real estate dreams into reality.

Welcome to Caleb Kercheval Real Estate Agency, your trusted partner in finding the perfect property in the enchanting region of Sag Harbor, New York. Located conveniently at 4098 Noyack Road, Caleb Kercheval is dedicated to providing exceptional real estate services to both buyers and sellers. With a deep understanding of the local market and a commitment to personalized service, our experienced team is here to guide you through every step of your real estate journey. Whether you're looking for a charming coastal home, a luxurious estate, or a promising investment property, Caleb Kercheval Real Estate Agency is here to make your dreams a reality. Visit us today and discover the unique charm and opportunities that Sag Harbor has to offer.

Welcome to Apples 2 Apples, your trusted partner in real estate and general contracting, located at 61 Wickatuck Drive, Sag Harbor, New York. Nestled in the heart of the Hamptons, our business is dedicated to transforming your real estate dreams into reality. Whether you're looking to buy, sell, or develop property, Apples 2 Apples offers expert guidance and personalized service every step of the way. With a deep understanding of the local market and a commitment to excellence, our team of experienced professionals provides comprehensive solutions tailored to your unique needs. From finding the perfect home or investment property to managing renovations and new constructions, we ensure quality and satisfaction in every project.