The 30 Best Island vacation rentals in New York

Welcome to Daniel Gale Sotheby’s International Realty, Shelter Island, NY, where your real estate journey begins. Located at 11 Grand Avenue, Shelter Island Heights, our office is at the heart of one of New York's most serene and picturesque locales. Under the expert guidance of Sales Manager Patricia Cosmadelis, our team is dedicated to providing unparalleled service in the Shelter Island area. Our office hours are Monday through Friday from 9:30 am to 3:30 pm, and on weekends from 10:00 am to 3:00 pm. We invite you to explore our exclusive Shelter Island listings, thoughtfully curated to meet diverse preferences and lifestyles. Each listing is provided by Daniel Gale Sotheby’s International Realty, ensuring you access to reliable and up-to-date property information.

Welcome to MVM Island Realty, your trusted partner in navigating the vibrant real estate market of Shelter Island, New York. Conveniently located at 6 South Ferry Road, our agency is committed to providing exceptional service and personalized attention to each of our clients. Whether you're searching for your dream home, a vacation getaway, or an investment property, our experienced team of local experts is here to guide you through every step of the process. At MVM Island Realty, we pride ourselves on our deep knowledge of the Shelter Island community and our dedication to making your real estate experience seamless and rewarding. Explore the unique charm and beauty of Shelter Island with us and discover why so many choose to call this special place home. Visit us today and let us help you find your perfect island property.

Welcome to Southampton Long Island Hotel - Your Southampton Escape, where comfort meets convenience in the heart of the Hamptons. Nestled at 450 County Road 39 5207, Southampton, New York, our charming hotel offers the perfect retreat for travelers seeking a relaxing getaway or an exciting adventure. Whether you're visiting for a weekend escape or an extended stay, our prime location provides easy access to the area's stunning beaches, vibrant cultural attractions, and exquisite dining options. At Southampton Long Island Hotel, we pride ourselves on delivering exceptional hospitality and personalized service. Our well-appointed rooms are designed with your comfort in mind, featuring modern amenities to ensure a restful stay. Begin your day with a refreshing dip in our outdoor pool or explore the picturesque surroundings with our complimentary bike rentals.

Welcome to Hamptons Vacation Inn, your ideal getaway located in the heart of the picturesque Hampton Bays, New York. Nestled at 177 West Montauk Highway, our charming lodging offers a perfect blend of comfort, convenience, and coastal charm. Whether you're seeking a relaxing retreat or an adventurous escape, our inn provides the perfect base for exploring the beautiful surroundings of the Hamptons. At Hamptons Vacation Inn, we pride ourselves on delivering exceptional hospitality and personalized service to make your stay truly memorable. Our well-appointed rooms are designed with your comfort in mind, featuring modern amenities and tasteful decor that reflect the serene ambiance of the area. Wake up to the gentle sounds of nature and enjoy a leisurely morning with a cup of coffee on your private balcony or patio.

House On Chase Creek is a charming lodging institution located at 3 Locust Avenue in Shelter Island Heights, New York. Situated in a picturesque setting, this cozy retreat offers a peaceful and tranquil atmosphere for guests to relax and unwind. The charming architecture and beautiful surroundings of Chase Creek provide a perfect backdrop for a memorable stay. With comfortable accommodations and top-notch amenities, guests can enjoy a truly delightful experience during their visit. Whether you're looking for a weekend getaway or an extended stay, House On Chase Creek is the perfect destination for a rejuvenating retreat.

The Pridwin Hotel & Cottages is a luxurious lodging institution located at 81 Shore Road, Shelter Island, New York, United States. The campus offers a serene atmosphere perfect for relaxation and rejuvenation. Guests can enjoy a water-view pool overlooking Crescent Beach, complimentary yoga sessions, tennis clinics, and access to the new Pridwin Spa for day spa treatments and massages. The Fitness Center is equipped with cardio and strength-training equipment for guests to use throughout their stay. Outdoor activities such as kayaking and stand-up paddleboarding are also available. The institution hosts special events like plein air landscape drawing and painting workshops, as well as Murder Mystery weekends with immersive storytelling and problem-solving activities. Complimentary high-speed WiFi is available throughout the grounds, and guests can enjoy daily breakfast at the Terrace restaurant. Transportation to Shelter Island is made easy with partnerships with Hampton Jitney and North Ferry, providing a convenient car-free travel option from New York City.

Winthrop Manor Ltd is a charming lodging establishment situated at 13 Winthrop Road in the picturesque town of Shelter Island Heights, New York. This historic manor offers a cozy and inviting atmosphere for guests looking for a relaxing getaway. The beautifully appointed rooms and suites provide a comfortable retreat, while the convenient location allows easy access to the island's attractions and activities. Whether you're seeking a romantic escape or a family vacation, Winthrop Manor Ltd is the perfect choice for your stay in Shelter Island Heights.

Shutters & Sails, LLC is a premier real estate agency located at 643 Equestrian Avenue in the beautiful town of Fishers Island, New York. Specializing in luxury waterfront properties, our dedicated team of professionals is committed to helping clients find their dream homes along the stunning coastlines of this exclusive island. With a focus on personalized service and attention to detail, Shutters & Sails, LLC is the go-to agency for those seeking a seamless and successful real estate experience. Contact us today to start your journey towards owning a piece of paradise on Fishers Island.

Mystic Isle Realty is a reputable real estate agency located at 1318 Central Avenue, Fishers Island, New York. Specializing in luxury properties and waterfront estates, their team of experienced agents are dedicated to helping clients find their dream home or investment property. With a strong focus on customer service and local market knowledge, Mystic Isle Realty is committed to providing personalized and professional assistance throughout the buying or selling process. Whether you are looking for a vacation home, a waterfront retreat, or a permanent residence, Mystic Isle Realty is the go-to agency for all your real estate needs on Fishers Island.

Penelope Moore Real Estate is a premier real estate agency located at 9 Grand Avenue in Shelter Island Heights, New York. Specializing in luxury properties in the Hamptons and surrounding areas, our team of experienced agents is dedicated to providing exceptional service to our clients. Whether you are looking to buy, sell, or rent a home, Penelope Moore Real Estate is committed to helping you achieve your real estate goals. Contact us today to learn more about our exclusive listings and personalized service.

M Wein Realty Inc. is a reputable real estate agency located at 34 North Ferry Road in Shelter Island, New York, United States. With a team of experienced and knowledgeable real estate agents, they specialize in helping clients buy, sell, and rent residential and commercial properties in the area. Whether you are looking for your dream home, a vacation rental, or a prime location for your business, M Wein Realty Inc. is dedicated to providing top-notch service and finding the perfect property to meet your needs. Contact them today to start your real estate journey.

Dering Harbor Real Estate is a prestigious real estate agency located at 182 North Ferry Road in Shelter Island Heights, New York. With a reputation for excellence and a commitment to personalized service, our experienced agents are dedicated to helping clients find their dream homes or investment properties. Whether you are looking to buy, sell, or rent, Dering Harbor Real Estate is your trusted partner in navigating the competitive real estate market. Contact us today to start your journey towards finding the perfect property in the beautiful surroundings of Shelter Island Heights, New York.

Havens House is a charming historic museum and tourist attraction located at 16 South Ferry Road on Shelter Island, in the picturesque state of New York, United States. This beautifully preserved institution offers visitors a glimpse into the island's rich history and culture, with exhibits showcasing artifacts, photographs, and documents from the past. Guests can explore the elegant rooms of the house, learn about the families who once lived there, and discover the stories that have shaped Shelter Island over the years. With its peaceful surroundings and fascinating displays, Havens House is a must-visit destination for history buffs and curious travelers alike.

Country Dream is a historic institution located at 258 Pine Island Turnpike in Warwick, New York. Originally founded in 1850, the building has seen various owners over the years, each adding their own unique touch to the establishment. From Wheeler Roe to Seely S Everett, the Country Dream has a rich history that dates back over a century. Today, the Country Dream is home to a charming restaurant that serves American traditional cuisine with a focus on homemade side dishes, freshly harvested produce, and delicious sauces. The menu features a variety of dishes that are sure to satisfy any craving, from hearty breakfast options to mouthwatering lunch specials.

Villa Koko is a trendy clothing store located at 65 Page Avenue in New York, United States. Our store offers a wide selection of stylish and chic clothing for men and women, ranging from casual wear to formal attire. Our knowledgeable staff is always on hand to help you find the perfect outfit for any occasion. Whether you're looking for the latest fashion trends or timeless classics, Villa Koko has something for everyone. Visit us today and elevate your wardrobe with our unique and fashionable pieces.

Fina's Farmhouse is a charming cafe, food store, and restaurant located at 20 Ellis Street in the heart of New York City. Our cozy and inviting farmhouse-style setting offers a unique dining experience where guests can enjoy delicious homemade meals made with fresh, locally-sourced ingredients. From hearty breakfast options to mouth-watering lunch and dinner selections, Fina's Farmhouse has something to satisfy every craving. Our store also offers a variety of specialty food items and gifts for purchase. Come visit us at Fina's Farmhouse for a taste of home-cooked comfort in the bustling city!

The Manor is a charming and cozy restaurant located at 917 Manor Road in New York, United States. Known for its delicious and diverse menu offerings, The Manor provides a warm and inviting atmosphere for guests to enjoy a memorable dining experience. Whether you're looking for a casual meal with friends or a special occasion dinner with loved ones, The Manor is the perfect destination. With attentive service and a welcoming ambiance, The Manor is sure to become your go-to spot for exceptional food and hospitality.

Majors Travel is a reputable travel agency located at 1192 Forest Avenue in New York, United States. With years of experience in the industry, Majors Travel offers a wide range of travel services including booking flights, hotels, car rentals, and vacation packages. Their team of knowledgeable and friendly travel agents are dedicated to helping clients plan their dream vacations with ease and convenience. Whether you're looking to explore exotic destinations or simply need assistance with travel arrangements, Majors Travel is committed to providing excellent customer service and creating unforgettable travel experiences for their clients. Contact Majors Travel today to start planning your next adventure!

Solamar Travel Bureau Inc is a premier travel agency located at 262 Arden Avenue in New York, United States. With years of experience in the travel industry, our dedicated team of professionals is committed to providing exceptional service and personalized travel experiences to our clients. Whether you're planning a relaxing beach getaway, an adventurous safari, or a romantic European vacation, Solamar Travel Bureau Inc has the expertise to make your travel dreams a reality. Contact us today to start planning your next unforgettable journey.

Princess Travel is a premier travel agency located at 289 Seaview Avenue in New York, United States. With a focus on providing exceptional service and unforgettable travel experiences, Princess Travel offers a wide range of services including booking flights, accommodations, tours, and more. Our team of experienced travel agents is dedicated to helping clients plan their dream vacations, whether it's a romantic getaway, a family holiday, or a solo adventure. Let Princess Travel take care of all your travel needs and make your next trip truly memorable.

United Travel Deals is a reputable travel agency located at 2655 Richmond Avenue in New York, United States. With years of experience in the travel industry, our team of experts is dedicated to providing the best deals and packages for all your travel needs. Whether you're planning a relaxing beach getaway, an adventurous hiking trip, or a romantic European vacation, we are here to help you find the perfect travel deal. Contact us today to start planning your next unforgettable journey!

Geo Travel is a premier travel agency located at 925 Coney Island Avenue in New York, United States. Specializing in providing top-notch travel services, Geo Travel offers a wide range of travel packages, including flights, accommodations, tours, and more. With a team of experienced travel experts, Geo Travel is dedicated to creating unforgettable travel experiences for its clients. Whether you're planning a relaxing beach getaway, an adventurous safari, or a cultural exploration, Geo Travel has the expertise to make your travel dreams a reality. Visit Geo Travel today and let us help you plan your next unforgettable journey.

Tulcingo Travel is a reputable travel agency located at 473 Saint Marks Place in New York, United States. With a team of experienced travel experts, Tulcingo Travel offers a wide range of travel services including booking flights, hotels, car rentals, and vacation packages. Whether you're planning a relaxing beach getaway or an adventurous trek through the mountains, Tulcingo Travel can help you create the perfect itinerary to suit your needs and budget. Visit us today and let us help you plan your next unforgettable travel experience.

Kathy Barzal Real Estate is a reputable real estate agency located at 113 New Dorp Plaza in New York, United States. With years of experience and expertise in the real estate industry, Kathy Barzal and her team provide top-notch services to help clients buy, sell, or rent properties in the New York area. Whether you are looking for a new home, investment property, or commercial space, Kathy Barzal Real Estate is dedicated to helping you find the perfect property to meet your needs. Contact them today to start your real estate journey with a trusted and reliable agency.

DiTommaso Real Estate is a reputable real estate agency located at 113 New Dorp Plaza in New York, United States. With a team of experienced and knowledgeable real estate professionals, DiTommaso Real Estate is dedicated to helping clients buy, sell, and rent properties in the New York area. Whether you are looking for a new home, investment property, or commercial space, DiTommaso Real Estate can assist you in finding the perfect property to meet your needs. Contact us today to learn more about our services and how we can help you achieve your real estate goals.

Located at 27-03 42nd Road in New York, United States, 27 on 27th is a prestigious real estate agency offering carefully crafted studio, one-bedroom, two-bedroom, and penthouse apartments in Long Island City. With upscale features, iconic skyline views, and attentive service, Heritage 27 on 27th provides a luxurious living experience. The community offers a variety of amenities and living spaces for residents to enjoy. Whether you are looking for a new home or simply want to learn more about the lifestyle at Heritage 27 on 27th, our leasing consultants are available to assist you. Come home to Heritage 27 on 27th and experience the best of urban living in New York City.

Lisa Juliano - DiTommaso Real Estate is a premier real estate agency located at 113 New Dorp Plaza in New York, United States. With years of experience and expertise in the real estate market, the team at Lisa Juliano - DiTommaso Real Estate is dedicated to helping clients buy, sell, and rent properties with ease. Whether you are looking for your dream home, an investment property, or commercial real estate, their knowledgeable agents are here to guide you every step of the way. Trust Lisa Juliano - DiTommaso Real Estate to provide you with top-notch service and exceptional results in all your real estate needs.

La Quinta Inn by Wyndham Queens in New York City offers comfortable and affordable lodging accommodations at 37-18 Queens Boulevard. This hotel is conveniently located in the bustling city, providing easy access to popular attractions, restaurants, and shopping areas. Guests can enjoy modern amenities, spacious rooms, and friendly service during their stay. Whether visiting for business or leisure, La Quinta Inn by Wyndham Queens is the perfect choice for a relaxing and enjoyable stay in the heart of New York City.

Harbor House Bed & Breakfast is a charming lodging establishment located at 1 Hylan Boulevard in New York, United States. Nestled in a picturesque setting, this cozy bed and breakfast offers a tranquil retreat for guests looking to relax and unwind. With comfortable accommodations, warm hospitality, and a delicious homemade breakfast served each morning, Harbor House is the perfect choice for a peaceful getaway in the bustling city. Whether you're visiting for business or pleasure, you'll feel right at home at Harbor House Bed & Breakfast.

Chateau De Capitaine is a charming restaurant located at 2570 Coney Island Avenue in New York, United States. This cozy establishment offers a unique dining experience with a menu inspired by French cuisine. The elegant decor and warm ambiance make it the perfect spot for a romantic dinner or a special celebration. Guests can enjoy a wide selection of delicious dishes prepared with fresh, high-quality ingredients by talented chefs. Whether you're looking for a relaxing meal with friends or a fine dining experience, Chateau De Capitaine is sure to impress.