TOP 10 Best Vacation cottage rentals in Woodstock, New York

The Woodstock Inn on the Millstream is a charming lodging establishment located at 48 Tannery Brook Road in Woodstock, New York. Nestled in the heart of the picturesque Catskill Mountains, this inn offers a peaceful retreat for guests looking to relax and unwind in a beautiful natural setting. The sound of the nearby Millstream adds to the tranquil atmosphere, while the cozy rooms and cottages provide a comfortable and inviting space for a restful night's sleep. Guests can enjoy a leisurely stroll through the lush gardens, or take a short walk to explore the quaint shops and art galleries in the historic town of Woodstock. With its serene surroundings and welcoming ambiance, The Woodstock Inn on the Millstream is the perfect destination for a peaceful getaway in upstate New York.

Rose Mountain Cottages, nestled in the heart of the central Catskills at 120 Creek Side Dr, Shandaken, NY, offers a serene escape into nature, rich with history and modern comforts. Originally built as Feitzingers Cabins in the late 1940s, this charming lodging facility has retained its traditional Bungalow Colony charm while undergoing thoughtful renovations to enhance comfort and convenience. Guests can choose from five unique cabins—Betty, Wendy, and Shelly, which are fully equipped for year-round stays with heating and insulation, as well as Georgie and Joan, available for warm-season rentals from May to October. All cabins are connected to a WiFi mesh network, ensuring guests stay connected during their retreat. Rose Mountain Cottages warmly welcomes well-behaved pets, encouraging a pet- and pollinator-friendly environment. Guests are asked to notify the establishment in advance and ensure their pets are under control and cleaned up after. For those pets that love to snuggle, bringing your own sheets is recommended.

Twin Gables of Woodstock is a charming lodging located at 73 Tinker Street in the picturesque town of Woodstock, New York. This historic institution offers cozy accommodations in a serene setting, perfect for a relaxing getaway in the heart of the Catskills. The Twin Gables of Woodstock provides a comfortable and welcoming atmosphere, with beautifully decorated rooms and modern amenities. Guests can enjoy the peaceful surroundings and explore the vibrant arts and culture scene of Woodstock, just steps away from the inn. Whether you're looking for a romantic retreat or a peaceful escape, Twin Gables of Woodstock is the perfect destination for your next vacation.

Woodstock Way Realty, LLC is a premier real estate agency located in Bethel, New York. Situated at 2027 New York 17B, this institution specializes in helping clients buy, sell, and rent properties in the beautiful Woodstock area. With a team of experienced and knowledgeable real estate agents, Woodstock Way Realty, LLC is dedicated to providing top-notch service and ensuring that clients find their dream home or investment property. Whether you are looking to buy a cozy cabin in the woods or sell a waterfront estate, Woodstock Way Realty, LLC is the go-to agency for all your real estate needs in the United States.

Woodstock Barn House is a charming institution located at 5 Downer Lane in the picturesque town of Woodstock, New York. As a real estate agency, we specialize in helping clients find their dream homes in this beautiful area. Additionally, we also operate as a travel agency, offering unique vacation rental options in and around Woodstock. Whether you are looking to buy a property or plan a relaxing getaway, Woodstock Barn House is here to assist you every step of the way. Experience the tranquility and charm of Woodstock with us.

Welcome to Ann Finneran, Woodstock Way Realty, LLC, your trusted partner in real estate located in the heart of Bethel, New York. Situated at 2027 New York 17B, our firm specializes in providing personalized and professional real estate services to meet all your buying, selling, and renting needs. With a deep understanding of the local market and a commitment to exceptional customer service, we are dedicated to helping you find the perfect property or achieve the best value for your sale. Whether you're seeking a serene retreat in the picturesque Catskills or looking to sell your home with confidence, Ann Finneran, Woodstock Way Realty, LLC is here to guide you every step of the way. Discover the difference of working with a team that truly cares about your real estate journey. Visit us today and let us make your real estate dreams a reality.

Villas in Woodstock is a charming lodging facility located at 18 Rock City Road in the picturesque town of Woodstock, New York. As a combination of a real estate and travel agency, Villas in Woodstock offers a unique experience for those looking to stay in the heart of the Catskills. With a variety of cozy villas available for short-term rentals, guests can enjoy the comforts of home while exploring all that Woodstock has to offer. Whether you're looking for a weekend getaway or a longer stay, Villas in Woodstock provides a peaceful and relaxing retreat for all travelers.

Glasco Woodstock is a premier real estate and travel agency located at 57 Smith Road in Saugerties, New York, United States. Specializing in helping clients find their dream homes in the picturesque Woodstock area, as well as offering expert travel planning services for those looking to explore the beautiful region. With a team of experienced professionals and a commitment to exceptional customer service, Glasco Woodstock is the go-to destination for all your real estate and travel needs in the Hudson Valley.

Peace of Mind Woodstock is a serene institution nestled in the heart of Woodstock, New York. With a mission to promote mental well-being and inner peace, this organization offers a variety of services such as therapy, meditation classes, and holistic healing treatments. Located at O. Box 43, Peace of Mind Woodstock is dedicated to helping individuals find balance and tranquility in their lives. Whether you are seeking support for anxiety, stress, or simply looking to enhance your spiritual growth, this institution provides a safe and nurturing environment for personal growth and self-discovery.

Welcome to Prestige Home Buyers, your trusted partner in selling your home quickly and hassle-free! Located at 198 Charter Oaks Avenue, Brentwood, New York, we specialize in providing homeowners across Long Island with a seamless and stress-free way to sell their properties for cash. At Prestige Home Buyers, we believe in empowering you to sell on your terms. Our process is designed to eliminate the traditional headaches associated with selling a home. We buy houses in any condition, and you don’t even need to clean or make repairs. Say goodbye to commissions, fees, and lengthy waiting periods. With us, you can get a no-obligation cash offer and close the deal in as little as five days!

Welcome to Samba Inn: Your Perfect Getaway in Jeffersonville, NY Nestled in the charming town of Jeffersonville, New York, Samba Inn offers a serene escape just two hours from the bustling streets of New York City. Located at 4893 New York 52, our cozy lodging provides the ideal base for exploring the scenic beauty and vibrant culture of the Catskills region.

Broadview Retreat House is a charming lodging facility located at 11 Broadview Road in the picturesque town of Woodstock, New York. Nestled in the heart of the United States, this institution offers a peaceful and serene retreat for those seeking a break from the hustle and bustle of everyday life. With comfortable accommodations and beautiful surroundings, guests can relax and rejuvenate in this tranquil setting. Whether you are looking for a weekend getaway or a longer stay, Broadview Retreat House is the perfect destination for those seeking rest and relaxation.

Coldwell Banker Village Green Realty is a premier real estate agency located in Woodstock, New York. Specializing in Upstate New York and Catskills real estate, our team of experienced agents knows the area like no one else. Whether you're looking to buy or sell a home, our experts are here to guide you every step of the way. With a focus on customer satisfaction, our agents are dedicated to finding the perfect home that meets all your needs. From in-town properties to rural retreats, we have the knowledge and expertise to help you find your dream home. Our team of professionals is backed by years of experience and a commitment to excellence, ensuring that your real estate experience is smooth and successful. Contact us today to discover the Coldwell Banker difference and find out how much your home is worth in today's market. Explore our enhanced listings and community guides to learn more about the Hudson Valley and Catskills regions. With offices in 8 counties, including Ulster, Greene, Dutchess, and Columbia, we have Upstate New York real estate covered. Trust Coldwell Banker Village Green Realty for all your real estate needs in the Hudson Valley and Catskills.

nestled in the woods, with views of the mountains or the river. If you're considering selling your Greene County home, reach out to us for expert advice and personalized service. Orange County NY Real Estate offers a mix of rural charm and suburban convenience, with easy access to NYC. Whether you're looking for a historic farmhouse in Warwick or a modern townhouse in Middletown, our agents in New Paltz NY can help you find the perfect Orange County property. If you're ready to sell your Orange County home, click below to learn more about our seller services and connect with an Orange County specialist. Putnam County NY Real Estate is perfect for those seeking a peaceful retreat from city life. With beautiful lakes, parks, and hiking trails, Putnam County offers an outdoor paradise just a short drive from NYC. Our New Paltz NY office can help you find the perfect Putnam County home for sale. Thinking of selling your Putnam County property? Click below to learn more about our seller services and connect with a Putnam County expert.