Shelter Island Vacation Packages 2026 from $561

Shelter Island flight + hotel vacation packages

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

Ink 48 Hotel

Manhattan

Save 100% on your flight

$561

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A 24-hour gym, valet parking, and concierge services are featured at this hotel. Traveling on business? Take advantage of the 5 conference rooms, express check-out, and laundry service. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Night Hotel Broadway

Manhattan

Save 100% on your flight

$722

per person

Oct 5 - Oct 10

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$755

per person

Oct 5 - Oct 8

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, dry cleaning, and luggage storage are also on offer.

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$734

per person

Oct 5 - Oct 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.

The Towers at Lotte New York Palace

Manhattan

Save 100% on your flight

$1,423

per person

Oct 2 - Oct 5

found 24 hours ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,230 nightly

$1,405 total

Jul 13 - Jul 14

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$96 nightly

$111 total

Jul 13 - Jul 14

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

Montauk Yacht Club

32 Star Island Rd Montauk NY

$766 nightly

$875 total

Jul 26 - Jul 27

Total with taxes and fees

This luxury 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.

On private beach

Pool

Sound View Greenport

58775 County Rd 48 Greenport NY

$552 nightly

$630 total

Aug 3 - Aug 4

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

Montauk Manor

236 Edgemere St. Montauk NY

$481 nightly

$549 total

Jul 27 - Jul 28

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.

Pool

Hot Tub

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$314 nightly

$361 total

Aug 12 - Aug 13

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

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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?

$561 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.