Shelter Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.
Top Shelter Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
CA $1,535
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
The Plaza, A Fairmont Hotel
Manhattan
CA $3,814
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Everything was fantastic and consistent with our prior experience at the plaza. Check-in was fast, the room was spotless, room service was quick, turn Service down was nice to have. Food offerings are a little limited after 10:30 am, but you’re in Manhattan and can step outside and go 10 feet to any number of great restaurants.
Reviewed on Aug 24, 2026
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
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.
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 Crescent Beach and Sunset Beach.
Coecles Harbor
When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Shelter Island Historical Society, some noteworthy sights in the nearby area.
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.
Shorewood
While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.
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 centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres 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.
Ready to book your vacation to Shelter Island?
Shelter Island Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $120
CA $138 total
Aug 26 - Aug 27
includes taxes & fees
8/10 Very good! (1,017 reviews)
"Needs to be updated badly. Would have spent more money to stay somewhere better."
Reviewed on Aug 23, 2026
Sound View Greenport
58775 County Rd 48 Greenport NY
CA $314
CA $477 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very good! (703 reviews)
"The property is well maintained and the location is perfect, however, there were some downsides during our stay. My fiancé, our dog, and I went to this hotel as it's a pet-friendly location, on their website they advertised amenities for pets (i.e, Yeti dog bowl(s), plush bed) but we never received ..."
Reviewed on Aug 24, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
CA $321
CA $393 total
Sep 14 - Sep 15
includes taxes & fees
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.
Stay near popular Shelter Island attractions
Wades Beach
10.0/10 (1 review)
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.
Shell Beach
10.0/10 (1 review)
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.
Shelter Island Historical Society
8.0/10 (1 review)
You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.
Mashomack Preserve
Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
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.
Shelter Island Whale's Tail
10.0/10 (1 review)
You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.
Menhadden Lane Beach
8.8/10 (3 reviews)
Why not spend a carefree afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
What to do in Shelter Island
Frequently asked questions
How much does a Shelter Island vacation package cost?
Offering great value package deals from CA $1,235 on Expedia, you'll be thrilled with how little a vacation to Shelter Island costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
The off-season is the best time to visit Shelter Island if you're trying to keep costs down. Another tip for getting cheap Shelter Island vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Shelter Island?
To get the most out of your Shelter Island vacation, we suggest staying for 5 days. Split your time between discovering Greenport Carousel, Bay Street Theatre and other top attractions, as well as experiencing neighbourhoods like Greenport West and The Heights. If you've got some spare time, add a tour or day trip to your Shelter Island vacation itinerary.
Is it worth booking a vacation package to Shelter Island?
It's no wonder a Shelter Island vacation is on the must-do list of many travellers. Well-known attractions like Shell Beach are just the beginning of what you can explore here.
How to find the best Shelter Island package deals?
Start your search for a Shelter Island package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shelter Island package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Shelter Island adventure off to a flying start.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Shelter Island?
If you're considering a spontaneous Shelter Island adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Shelter Island?
- Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Shelter Island.
- Budget wisely: On top of the cost of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Shelter Island.
- Decide how long to go away for: Now that you're up to speed on Shelter Island, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Shelter Island vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
