Shelter Island Vacation Packages

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Flight and hotel packages to Shelter Island

Price found within the past 48 hours. Click for updated prices.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip 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, express check-in, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 8 - Aug 11
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.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 5 - Aug 11
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
A restaurant and a rooftop terrace are featured at this hotel. WiFi in public areas is free. A business center, a terrace, and luggage storage are also on offer.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.
RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, express check-out, and dry cleaning are also on offer.

Top Shelter Island hotel deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is $511 per night
$511
per night
May 30 - May 31
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.
Pet friendly
Breakfast available
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
The price is $89 per night
$89
per night
May 26 - May 27
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Pet friendly
Parking included
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
The price is $168 per night
$168
per night
May 28 - May 29
This Tudor aparthotel features a full-service spa, 3 outdoor tennis courts, and a restaurant. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.
Pool
Spa
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
Free Cancellation
The price is $197 per night
$197
per night
Jun 4 - Jun 5
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. A garden is provided and the front desk is staffed around-the-clock.
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free Cancellation
The price is $159 per night
$159
per night
May 27 - May 28
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.
Pet friendly
Breakfast available
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
The price is $155 per night
$155
per night
May 30 - May 31
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, free newspapers, and barbecue grills are also on offer.
Pet friendly
Pool
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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 in Shelter Island

Image for Gardiner's Bay Country Club

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.

Gardiner's Bay Country Club
Image for Shelter Island Historical Society

Shelter Island Historical Society

4/5(1 review)

You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society
Image for Shell Beach

Shell Beach

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.

Shell Beach

Frequently asked questions

How much are vacation packages to Shelter Island?
$459 is all you’ll need for an exhilarating break in Shelter Island. Bundle your flights and hotel into a Travelocity package and watch how the savings start to grow. With prices this good, traveling has never been so accessible.
Where can I get the best vacation package deals for Shelter Island?
With as many as 400 airline partners and 1,000,000 hotels across the world, it’s hard to top Travelocity. Look through our extensive range and create the perfect Shelter Island package deal. Don’t you love it when planning a trip is that easy?
Why should I book my Shelter Island vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you’ll always get the best deal available.
Can I save money on my Shelter Island car rental if I bundle it with hotels and flights?
Combining your bookings into a Shelter Island vacation package will leave you with a nice chunk of spare change. You can book a car and flight; a flight, car and hotel; or a car and hotel. You won’t find a better way to discover the greater Shelter Island area than with your own rental car. You can also add experiences and activities to your Travelocity package.
What is the best time of year to go to Shelter Island?
It comes down to whether you prefer to save cash or visit Shelter Island at its most exciting. The quietest time to see this part of the world is January, October and December. If you’d like to experience this destination at its busiest, consider May, June and July. More interested in saving your hard-earned money? The most affordable month is . usually has the highest prices.