Shelter Island Vacation Packages 2026 from $648

Shelter Island flight + hotel vacation packages

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

The Wayne Inn

Save 100% on your flight

$648

per person

Jul 17 - Jul 20

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

A restaurant, free self parking, and a 24-hour front desk are among this hotel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.

2 bedroom luxury Empire State VIEW

Manhattan

$3,110

per person

Jun 21 - Jun 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

The Towers at Lotte New York Palace

Manhattan

$2,838

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) 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.

1 Hotel Brooklyn Bridge

$1,599

per person

Jul 24 - Jul 27

found 11 hours 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.

Topping Rose House

$3,797

per person

Aug 3 - Aug 7

found 9 hours ago

Roundtrip flight included

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$585 nightly

$669 total

May 17 - May 18

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.

Montauk Manor

236 Edgemere St. Montauk NY

$185 nightly

$212 total

May 21 - May 22

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.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$80 nightly

$92 total

May 20 - May 21

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.

Montauk Yacht Club

32 Star Island Rd Montauk NY

$347 nightly

$396 total

May 17 - May 18

Total with taxes and fees

This 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.

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$182 total

May 17 - May 18

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. 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. There's a garden and multilingual staff can provide around-the-clock assistance.

Sound View Greenport

58775 County Rd 48 Greenport NY

$370 nightly

$422 total

May 19 - May 20

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.

Don't see what you're looking for?

See all available properties in Shelter Island

View all properties

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.

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.

Frequently asked questions

How much are vacation packages to Shelter Island?

$648 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.