Shelter Island Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.5-star property
Ink 48 Hotel
Manhattan
8.4/10 Very Good! (1,767 reviews)
Dec 9 - Dec 14
5 night stay
Atlanta (ATL) to New York (JFK)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,441, price is now $1,400 per person
$1,400
per person
found 1 day ago
A very friendly hotel and insane views from the room
Reviewed on Sep 17, 2026
Top rated hotels for your Shelter Island vacation package
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
15.48 mi from city center
$93 nightly
The price is $107 total per night
$107 total
Oct 14 - Oct 15
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex features free WiFi in public areas and a picnic area. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area.
Pet friendly
Parking included
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
18.43 mi from city center
$425 nightly
The price is $486 total per night
$486 total
Sep 30 - Oct 1
Total with taxes and fees
Guests of Gurney's Montauk Resort & Seawater Spa have access to a private beach, a full-service spa, and an indoor pool. The front desk is staffed 24/7 to help with securing valuables, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a 24-hour gym, meeting rooms, and a conference center.
On private beach
Pool
Sound View Greenport
58775 County Rd 48 Greenport NY
3.59 mi from city center
$264 nightly
The price is $302 total per night
$302 total
Oct 18 - Oct 19
Total with taxes and fees
Guests of Sound View Greenport enjoy features like a private beach, free WiFi in public areas, and conference space. Self parking is available for USD 29 per night. The front desk is staffed 24 hours a day to help with concierge services and luggage storage. Other amenities at this beach hotel include a seasonal outdoor pool, a terrace, and a banquet hall.
On private beach
Pool
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.
Things to do
Half-Day Private Long Island Wine Tour Experience
$290
per adult
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