Shelter Island Vacation Packages 2026 from $808

Shelter Island flight + hotel vacation packages

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

Night Hotel Broadway

Manhattan

Save 100% on your flight

$808

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.

NEW YORKER BY LOTTE HOTELS

Manhattan

$876

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This Art Deco hotel features 3 restaurants, a bar/lounge, and a gym. A 24-hour business center, a coffee shop, and a terrace are also on offer.

1 Hotel Brooklyn Bridge

Save 100% on your flight

$2,067

per person

Dec 22 - Dec 27

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.

The Inn At Fox Hollow Hotel

Save 100% on your flight

$875

per person

Dec 24 - Dec 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

33 Hotel, New York City, Seaport

Manhattan

Save 100% on your flight

$1,113

per person

Dec 22 - Dec 27

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. WiFi in public areas is free. There's dry cleaning and multilingual staff can provide around-the-clock assistance.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$436 nightly

$498 total

Nov 8 - Nov 9

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.

On private beach

Pool

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$224 nightly

$258 total

Nov 1 - Nov 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.

On private beach

Pool

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$89 total

Oct 19 - Oct 20

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.

Pet friendly

Parking included

Offshore Montauk

71 S Emerson Ave Montauk NY

$176 nightly

$201 total

Nov 1 - Nov 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.

Pool

Pet friendly

The Atlantic Hotel

1655 County Road 39 Southampton NY

$129 nightly

$147 total

Oct 28 - Oct 29

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.

Pool

Pet friendly

Sound View Greenport

58775 County Rd 48 Greenport NY

$198 nightly

$226 total

Nov 1 - Nov 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.

On private beach

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.

Stay near popular Shelter Island attractions

A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)

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.

See properties

Frequently asked questions

How much are vacation packages to Shelter Island?

$808 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.