Shelter Island Vacation Packages 2026 from $364

Shelter Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Grand Central New York

Manhattan

$364

per person

Apr 6 - Apr 9

found 1 day ago

Roundtrip 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.

OYO Times Square

Manhattan

$542

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, WiFi in public areas, and express check-out. Dry cleaning, luggage storage, and laundry facilities are also on offer.

Hotel Riu Plaza Manhattan Times Square

Manhattan

$863

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This property features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.

NobleDEN Hotel

Manhattan

$904

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

INNSiDE by Meliá New York Nomad

Manhattan

$941

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

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.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$363 nightly

$415 total

Feb 22 - Feb 23

Total with taxes and fees

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.

Sound View Greenport

58775 County Rd 48 Greenport NY

$174 nightly

$199 total

Mar 15 - Mar 16

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.

Montauk Manor

236 Edgemere St. Montauk NY

$133 nightly

$152 total

Mar 1 - Mar 2

Total with taxes and fees

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.

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

Get rates

This hotel features an indoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$91 total

Feb 15 - Feb 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Pet friendly

Parking included

Hyatt Place Long Island East End

451 East Main Street Riverhead NY

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$135 total

Mar 3 - Mar 4

Total with taxes and fees

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.

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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

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.

Man watching sailboat on Long Island Sound

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.

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Frequently asked questions

How much are vacation packages to Shelter Island?

$364 is all you need to spend for an amazing escape in Shelter Island. Bundle your flights and hotel into a Travelocity package and see your savings grow. With these kinds of prices, you'll want to start packing your suitcase now!

Where can I get the best vacation package deals for Shelter Island?

You'll find fantastic Shelter Island package deals with Travelocity. Pick from as many as 400 air carriers and 1,000,000 properties worldwide and turn those travel dreams into reality.

Why should I purchase my Shelter Island vacation package via Travelocity?

From our 24/7 customer support to our range of amazing destinations, we are committed to fulfilling your vacation dreams. All you have to do is click and book — our Price Match Guarantee will make sure you lock in the lowest price.

Can I save money on my Shelter Island car rental if I combine it with my hotel or flight?

You certainly can with our Shelter Island vacation packages. With one of these, there are lots of ways to stretch your vacation budget further. Combine any two or more car, flight, hotel and tour bookings and see the savings start to pile up. With your own ride, all the key sights around Shelter Island are within reach.