Title: Explore Shelter Island Vacation Book from $349 | Expedia.com [Shelter Island Travel Guide](https://expedia.com/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.com/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.com/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Car Rentals in Shelter Island](https://expedia.com/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Shelter Island Vacations from $349 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Shelter Island Vacation Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like [67 Steps Beach](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Railroad Museum of Long Island](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) and [Kontokosta Winery](https://www.expedia.com/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction). Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia. ## The Latest Shelter Island vacation packages Price found within the past 48 hours. Click for updated prices. ![The Westin New York Grand Central](https://images.trvl-media.com/lodging/6000000/5450000/5445500/5445478/02061152_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin New York Grand Central Manhattan Save 100% on your flight $349 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9/10 Wonderful! (3,569 reviews) I had a wonderful time at the Westin Grand Central. The rooms were clean and neat. The service was amazing. The breakfast buffet was a little overpriced, but The quality was excellent. To make it even more amazing, Eve Melendez and her team had a wonderful gift and a card my daughter when we arrived. She was amazing throughout our trip to New York City. Jose from concierge went above and beyond to help us get to where we need to be! Especially some last-minute pizza from uncle Paul’s. Thank you so much to the rockstar team at the Westin!! we will be back! Reviewed on Feb 6, 2026 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan $394 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April. Reviewed on Feb 6, 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan $487 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.2/10 Wonderful! (3,348 reviews) The staff was nice and the rooms were clean! Great place! Reviewed on Feb 6, 2026 ![The Inn At Fox Hollow Hotel](https://images.trvl-media.com/lodging/1000000/880000/871900/871849/9f9215cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn At Fox Hollow Hotel $481 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.2/10 Wonderful! (1,002 reviews) Rooms Property were Fantastic ! Reviewed on Feb 6, 2026 ![Mountain Springs Lake Resort](https://images.trvl-media.com/lodging/34000000/33270000/33260600/33260524/3c4b3304_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountain Springs Lake Resort $413 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (234 reviews) The staff was friendly and helpful. They were great! Reviewed on Feb 2, 2026 Don't see what you're looking for? See all available trips from Columbus to Shelter Island [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-07/2026-03-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=LGA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Where to stay in Shelter Island Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. [Learn more about Shelter Island](https://expedia.com/Shelter-Island.dx157359) ![Center console boat on Long Island, NY. Photographed by drone.](https://images.trvl-media.com/place/553248635976481903/93829460-9892-494c-803a-a3af6b3b8523.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Silver Beach While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach. [Find hotel + flight trips in Silver Beach](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Silver%20Beach&DestID=553248635976481903&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.](https://images.trvl-media.com/place/553248635976481214/0fd5766e-1ec1-4630-87ca-616953333ece.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Menantic Creek If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach. [Find hotel + flight trips in Menantic Creek](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Menantic%20Creek&DestID=553248635976481214&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.](https://images.trvl-media.com/place/553248635976480820/ef16583d-a1b3-4f29-8d9e-0f21fcceaafc.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Coecles Harbor When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area. [Find hotel + flight trips in Coecles Harbor](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Coecles%20Harbor&DestID=553248635976480820&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water](https://images.trvl-media.com/place/553248635976470037/504e907d-021d-4378-950f-32bb724622a2.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hay Beach Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. [Find hotel + flight trips in Hay Beach](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Hay%20Beach&DestID=553248635976470037&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial Views of Mamaroneck, New Rochelle, and Larchmont](https://images.trvl-media.com/place/553248635976481937/9210af7b-6de4-447d-b525-19512b2b53b1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shorewood While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Shell Beach and Shelter Island Historical Society. [Find hotel + flight trips in Shorewood](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Shorewood&DestID=553248635976481937&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Shelter Island ![Colorful pebbles and shells on a beach](https://images.trvl-media.com/place/553248621554204761/5a57054c-a374-4fe2-8982-2385bf184bb1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Shell Beach Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.com/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) ![Man watching sailboat on Long Island Sound](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wades Beach Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. [](https://expedia.com/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) #### Gardiner's Bay Country Club Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. [](https://expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) ## Shelter Island Hotel Deals ![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gurney's Montauk Resort & Seawater Spa 290 Old Montauk Highway Montauk NY $390 nightly $446 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (722 reviews) Room was spotless, staff were great and the resort is top notch!! Reviewed on Feb 2, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true®ionId=157359) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sound View Greenport 58775 County Rd 48 Greenport NY $158 nightly $180 total Feb 22 - Feb 23 Total with taxes and fees 8.4/10 Very Good! (609 reviews) This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ... Reviewed on Jan 10, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true®ionId=157359) ![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Montauk Manor 236 Edgemere St. Montauk NY $156 nightly $178 total Feb 23 - Feb 24 Total with taxes and fees 9/10 Wonderful! (1,291 reviews) The room was lovely, the little kitchenette is great. Very quiet and I love the balcony. The staff are great and the restaurant staff at Montis are fantastic Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=12694044&PinnedHotelID=12694044&HadPinnedHotel=true®ionId=157359) [See all 4,689 properties in Shelter Island](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=157359) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Find the Best Shelter Island Vacation Packages ### Things to do near Shelter Island Shelter Island offers a perfect getaway for outdoor enthusiasts and couples alike, featuring activities like golfing, skiing, and music concerts. Enjoy a relaxing beach experience with beach chairs for your comfort. Whether you're planning a day trip or a longer vacation, Shelter Island provides a charming atmosphere for those seeking a romantic beach retreat. **Shopping** If you're up for a drive, you can find great shopping options at the [Greenport Farmers' Market](https://www.expedia.com/Greenport-Farmers-Market-Greenport.d553248621532665744.Vacation-Attraction), located 3 miles away, for fresh local produce and unique gifts. [The Style Bar](https://www.expedia.com/The-Style-Bar-Sag-Harbor.d553248621532665737.Vacation-Attraction) and [BookHampton](https://www.expedia.com/BookHampton-Sag-Harbor.d553248621532665731.Vacation-Attraction), both 5 miles away, offer stylish apparel and a cozy selection of books, respectively. **Recreation** At [Bay Street Theatre](https://www.expedia.com/Bay-Street-Theatre-Sag-Harbor.d6326787.Vacation-Attraction), enjoy a captivating performance that blends culture and entertainment, creating a romantic atmosphere for couples or families. [Noyac Golf Club](https://www.expedia.com/Noyac-Golf-Club-Sag-Harbor.d6064499.Vacation-Attraction) offers a refreshing outdoor experience with its scenic golf course, while [Cedar Point County Park](https://www.expedia.com/Cedar-Point-County-Park-East-Hampton.d6326834.Vacation-Attraction) provides serene trails perfect for wellness and relaxation in nature. **Adventure** At [Splish Splash Water Park](https://www.expedia.com/Splish-Splash-Water-Park-Calverton.d6173416.Vacation-Attraction), located 23 miles from Shelter Island, enjoy thrilling water slides and family-friendly attractions for an exciting day out. For arcade fun, [Stay and Play LLC](https://www.expedia.com/Stay-And-Play-LLC-Old-Saybrook.d553248621532665775.Vacation-Attraction), 16 miles away, offers games and activities perfect for adventurous families. Explore the scenic [Walking Dunes Trailhead](https://www.expedia.com/Walking-Dunes-Trailhead-Montauk.d553248633992587102.Vacation-Attraction), also 16 miles away, for a refreshing hike. **Nightlife** Shelter Island offers a laid-back nightlife with cozy bars and intimate lounges. Enjoy live music at local venues, sip craft cocktails at waterfront spots, or unwind at a beach bonfire. The atmosphere is relaxed, perfect for mingling with locals and fellow travelers under the stars. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Shelter Island Located in New York, Shelter Island is a charming destination perfect for outdoor and romantic beach vacations. Visitors can explore beautiful spots like Crescent Beach and Hay Beach, alongside historic buildings and urban parks. The area offers a rich blend of culture and outdoor experiences, making it ideal for travelers seeking relaxation and adventure in a picturesque setting. - **[67 Steps Beach: ](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction)** Experience the serene beauty of 67 Steps Beach, just 4 miles from Shelter Island. With its inviting beach vibes, it's a perfect spot for sunbathing, swimming, or a peaceful stroll along the shore, offering a relaxing escape into nature. - **[Gardiner's Bay Country Club: ](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction)** Nestled within Shelter Island, Gardiner's Bay Country Club is a golfer's paradise. Enjoy a round of golf on its stunning course, surrounded by picturesque views and lush landscapes, making it an ideal spot for both seasoned players and beginners alike. - **[Orient Point County Park: ](https://www.expedia.com/Orient-Point-County-Park-Orient.d553248621532665781.Vacation-Attraction)** Located 8 miles from Shelter Island, Orient Point County Park is a family-friendly urban park. With ample outdoor activities, picnic areas, and scenic views, it’s a great destination for families looking to enjoy nature and city vibes simultaneously. ### Best time to go to Shelter Island The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 35.6°F (2.0°C) | Light Rain | Mostly Sunny | Average | Moderately Low | | February | 35.8°F (2.1°C) | Light Rain | Mostly Cloudy | Average | Moderately Low | | March | 39.7°F (4.3°C) | Light Rain | Mostly Sunny | Average | Moderately Low | | April | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Average | Average | | May | 55.8°F (13.2°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.9°F (18.3°C) | Light Rain | Mostly Sunny | High | Moderately High | | July | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | High | Moderately High | | August | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | High | Moderately High | | September | 68.2°F (20.1°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.7°F (15.4°C) | Light Rain | Mostly Sunny | Low | Average | | November | 49.6°F (9.8°C) | Light Rain | Mostly Sunny | Low | Average | | December | 42.1°F (5.6°C) | Light Rain | Mostly Cloudy | Low | Average | ### Tips to save on your trip to Shelter Island - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Shelter Island. - Consider traveling to Shelter Island during the low season (January to March) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Shelter Island Beach Vacation There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (1 mile away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach. ## Shelter Island Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 1,350 | | Max Temp Winter | 40ºF | | Max Temp Summer | 75ºF | | Top Sights | [Wolffer Estates Vineyard](https://www.expedia.com/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction), [East Hampton Main Beach](https://www.expedia.com/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction) and [67 Steps Beach](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Shelter Island vacation package cost? ### What are the cheapest months to go to Shelter Island? ### How many days is enough for Shelter Island? ### Is it worth booking a vacation package to Shelter Island? ### How to find the best Shelter Island package deals? ### Is it cheaper to book a Shelter Island vacation as a package? ### When to book a vacation package to Shelter Island? ### How to plan a trip to Shelter Island? > 1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Shelter Island. > 2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Shelter Island. > 3. Organize your Shelter Island getaway with Expedia's [trip planning tool](https://www.expedia.com/why/trip-planning): Look for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Shelter Island together. > 4. Decide your trip length: Think about how much time you want to spend exploring Shelter Island. Plan your days so you can get to all the attractions and activities you're interested in without rushing. > 5. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, lock in the right Shelter Island vacation package for you. > 6. Book any excursions or activities: Now to the fun part — organizing everything you want to do and see. Explore some of the best [things to do in Shelter Island](https://www.expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities) in Shelter Island and book your tickets early to save time (and maybe some cash too!). ### Does Expedia offer Book Now, Pay Later Shelter Island vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hotels near Shelter Island Historical Society ](https://www.expedia.com/Shelter-Island-Historical-Society-Hotels.0-l553248635961235094-0.Travel-Guide-Filter-Hotels) - [Hotels near Havens House ](https://www.expedia.com/Havens-House-Hotels.0-l6232745-0.Travel-Guide-Filter-Hotels) - [Hotels near Sylvester Manor ](https://www.expedia.com/Sylvester-Manor-Hotels.0-l6282169-0.Travel-Guide-Filter-Hotels) - [Hotels near Shelter Island Whale's Tail ](https://www.expedia.com/Shelter-Island-Whales-Tail-Hotels.0-l553248621554204762-0.Travel-Guide-Filter-Hotels) - [Hotels near Menantic Creek ](https://www.expedia.com/Menantic-Creek-Shelter-Island-Hotels.0-n553248635976481214-0.Travel-Guide-Filter-Hotels) - 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[Wades Beach ](https://www.expedia.com/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction) - [Mashomack Preserve ](https://www.expedia.com/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction) - [Sunset Beach ](https://www.expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction) - [Shell Beach ](https://www.expedia.com/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction) - [Crescent Beach ](https://www.expedia.com/Crescent-Beach-Shelter-Island-Heights.d553248621554204758.Vacation-Attraction) - [Gardiner's Bay Country Club ](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction) - [Visit Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights.dx183716) - [Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) - [Camera Obscura ](https://www.expedia.com/Camera-Obscura-Greenport.d6326819.Vacation-Attraction) - [Greenport Vacations ](https://www.expedia.com/Greenport.d110728.Destination-Travel-Guides) - [Greenport Farmers' Market ](https://www.expedia.com/Greenport-Farmers-Market-Greenport.d553248621532665744.Vacation-Attraction) - [Norman E. Klipp Marine Park ](https://www.expedia.com/Norman-E-Klipp-Marine-Park-Greenport.d553248626388141305.Vacation-Attraction) - [Visit Greenport ](https://www.expedia.com/Greenport.dx110728) - [Car rentals near Shelter Island Heights ](https://www.expedia.com/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide) - [Car rentals near Dering Harbor ](https://www.expedia.com/Car-Rentals-In-Dering-Harbor.d553248634998885605.Car-Rental-Guide) - [Car rentals near Greenport ](https://www.expedia.com/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide) - [Shelter Island Heights Vacation Rentals ](https://www.expedia.com/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals) - [Greenport Vacation Rentals ](https://www.expedia.com/Greenport-Vacation-Rentals.d110728.Travel-Guide-VacationRentals) - [Things to do in Greenport ](https://www.expedia.com/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app