Shelter Island Vacation Packages 2026 from $435

Shelter Island flight + hotel vacation packages

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

Hotel St. James

Manhattan

$435

per person

Apr 24 - Apr 28

found 2 days ago

Roundtrip flight included

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

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.

1 Hotel Central Park

Manhattan

Save 100% on your flight

$2,224

per person

May 16 - May 23

found 16 hours 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, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

Park Lane New York

Manhattan

Save 100% on your flight

$606

per person

Apr 23 - Apr 26

found 15 hours ago

Roundtrip flight included

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

This luxury hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a garden, and a lobby fireplace are also on offer.

The Towers at Lotte New York Palace

Manhattan

Save 100% on your flight

$2,802

per person

May 16 - May 23

found 16 hours ago

Roundtrip flight included

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

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.

WestHouse New York

Manhattan

$793

per person

May 13 - May 17

found 1 day ago

Roundtrip flight included

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

This hotel features a 24-hour gym and a rooftop terrace. Business travelers can take advantage of the 24-hour business center. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$400 nightly

$457 total

Mar 26 - Mar 27

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

Montauk Manor

236 Edgemere St. Montauk NY

$148 nightly

$169 total

Mar 15 - Mar 16

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

$164 nightly

$189 total

Apr 2 - Apr 3

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

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

Get rates

This hotel features an indoor pool and a hot tub. A terrace, a picnic area, and luggage storage are also on offer.

Pool

Hot Tub

Sound View Greenport

58775 County Rd 48 Greenport NY

$178 nightly

$203 total

Mar 26 - Mar 27

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

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$151 total

Apr 5 - Apr 6

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.

Pool

Pet friendly

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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.

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?

$435 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.