Shelter Island Vacation Packages 2026 from $583

Shelter Island flight + hotel vacation packages

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

Feather Factory

Queens

Save 100% on your flight

$583

per person

Nov 18 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

Free WiFi in public areas, a convenience store, and luggage storage are available at this hotel. A safe deposit box is provided and the front desk is staffed around-the-clock.

Seven Beach Lane

Save 100% on your flight

$1,231

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

San Juan (SJU) to New York (JFK)

This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,803

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip 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.

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$1,267

per person

Nov 16 - Nov 22

found 2 days 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, dry cleaning, and luggage storage are also on offer.

Hotel St. James

Manhattan

Save 100% on your flight

$1,002

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.

Top Shelter Island hotels deals

Sound View Greenport

58775 County Rd 48 Greenport NY

$286 nightly

$327 total

Oct 1 - Oct 2

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.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$93 nightly

$107 total

Sep 28 - Sep 29

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 is also provided.

The Atlantic Hotel

1655 County Road 39 Southampton NY

$165 nightly

$188 total

Oct 1 - Oct 2

Total with taxes and fees

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.

Offshore Montauk

71 S Emerson Ave Montauk NY

$321 nightly

$366 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. Express check-out and luggage storage are also provided.

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$808 nightly

$923 total

Sep 30 - Oct 1

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.

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$266 nightly

$306 total

Sep 1 - Sep 2

Total with taxes and fees

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.

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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.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)

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.

See properties

Frequently asked questions

How much are vacation packages to Shelter Island?

$583 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.