Shelter Island Trips (flight + hotel)
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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
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.
Top hotels in Shelter Island
Montauk Yacht Club
32 Star Island Rd, Montauk, NY
The price is P14,468 per night from 6 May to 7 May
P14,468
P16,530 total
includes taxes & fees
May 6 - May 7
8.4/10 Very Good! (999 reviews)
"The staff was kind and very hospitable. Very beautiful environment and clean place to stay."
Reviewed on Apr 29, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is P4,972 per night from 4 May to 5 May
P4,972
P5,717 total
includes taxes & fees
May 4 - May 5
7.6/10 Good! (950 reviews)
"Convenient, great value"
Reviewed on Apr 27, 2025
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is P11,116 per night from 4 May to 5 May
P11,116
P13,747 total
includes taxes & fees
May 4 - May 5
8.6/10 Excellent! (1,001 reviews)
"Spa was fantastic, rooms are nothing extravagant but clean and well maintained. Everyone was polite, great stay"
Reviewed on Apr 29, 2025
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.
Popular places to visit
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.
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Visit Sierra MadreVisit AnaheimVisit Santa Rosa BeachVisit Sun ValleyVisit SalidaVisit Niagara FallsVisit Santa YnezVisit MontaukVisit River RanchVisit Sequoia National ParkVisit Mountain ViewVisit Devils TowerVisit Laguna BeachVisit White PlainsVisit Kiawah IslandVisit HiloVisit SavannahVisit Grand Canyon
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.