
Deals on vacations and trips to Shelter Island
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Shelter Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Grand Central New York
Manhattan
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
A 24-hour gym, valet parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas.

1 Hotel Brooklyn Bridge
Save 100% on your flight
per person
Jul 26 - Jul 30
found 17 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

The Fifth Avenue Hotel
Manhattan
Save 100% on your flight
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

INNSiDE by Meliá New York Nomad
Manhattan
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
per person
Jun 7 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Top Shelter Island hotels deals

Montauk Yacht Club
32 Star Island Rd, Montauk, NY
The price is $296 per night
$296
includes taxes & fees
$259 per night
May 4 - May 5
This hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi in public areas. Enjoy the 2 outdoor pools and get free self parking.

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
The price is $102 per night
$102
includes taxes & fees
$89 per night
May 4 - May 5
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.

Montauk Manor
236 Edgemere St., Montauk, NY
The price is $208 per night
$208
includes taxes & fees
$182 per night
May 5 - May 6
3 outdoor tennis courts, an indoor pool, and a 24-hour gym are all featured at this smoke-free aparthotel. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a restaurant and a bar/lounge for dining and drinks, and also a hot tub on site.

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
The price is $661 per night
$661
includes taxes & fees
$579 per night
May 15 - May 16
This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
Free Cancellation
Reserve now, pay when you stay
The price is $226 per night
$226
includes taxes & fees
$196 per night
May 4 - May 5
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

Hyatt Place Long Island East End
451 East Main Street, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
The price is $170 per night
$170
includes taxes & fees
$149 per night
May 4 - May 5
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
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
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 Historical Society
4/5(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.
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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