Shelter Island Vacation Package Deals & Trips

Choose one or more items to build your trip:

Top Shelter Island Flight + Hotel Vacation Package Deals

JW Marriott Essex House New York
The Plaza Hotel
The Westin New York at Times Square
New York Marriott Marquis
Hotel Hugo

Top Hotels in Shelter Island

Waterfront House With Dock And Private Beach
Waterfront House With Dock And Private Beach
Shelter Island, NY
5/5 Exceptional! (12 reviews)
A wonderful stay
"We had a wonderful stay in Shleter island and are definitely planning to be back. The house is beautiful, very well equipped, comfortable and welcoming. The hosts were helpful and the location is amazing."

Reviewed on Oct 12, 2021

Waterfront House With Dock And Private Beach
Shelter Island - Newly Renovated Home with Heated Outdoor Pool
Shelter Island - Newly Renovated Home with Heated Outdoor Pool
Shelter Island, NY
5/5 Exceptional! (1 review)
Great stay in Shelter!
"Spent a great week with friends and my pups here. Owners and property manager were great and super responsive. Beautiful backyard with big pool and super close to Wade’s beach. The house has everything you need for a perfect stay! I will be back!"

Reviewed on Aug 30, 2021

Shelter Island - Newly Renovated Home with Heated Outdoor Pool
Paradise found on Shelter Island
Paradise found on Shelter Island
Shelter Island, NY
5/5 Exceptional! (4 reviews)
Lovely stay for a fall wedding
"We spent a long weekend here while attending my brother's wedding. The house was perfectly set up with split bedrooms allowing us to keep our noisy kids separate from other guests who wake up later. The house was perfectly clean upon arrival and the owner even laid out snacks and fruit which was ..."

Reviewed on Oct 1, 2021

Paradise found on Shelter Island
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.

Shelter Island Beach Vacation

There's nothing that can beat a Shelter Island vacation. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favorite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 1 mile (2 km) from downtown. However, you'll also discover a fantastic range of Shelter Island vacation deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

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