Shelter Island Vacation Packages 2026 from $545

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

$545

per person

Jul 17 - Jul 20

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to New York (JFK)

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.

Seven Beach Lane

$1,403

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The Towers at Lotte New York Palace

Manhattan

$3,001

per person

Jun 26 - Jul 1

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) 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.

42 Hotel

Save 100% on your flight

$727

per person

Jul 9 - Jul 14

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, a gym, and a bar/lounge. Self parking, a lobby fireplace, and dry cleaning are also offered.

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$978

per person

Jul 3 - Jul 7

found 1 day ago

Roundtrip flight included

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

This property 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.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$478 nightly

$546 total

May 5 - May 6

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

$168 nightly

$192 total

Apr 27 - Apr 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

Sound View Greenport

58775 County Rd 48 Greenport NY

$252 nightly

$288 total

May 3 - May 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 Yacht Club

32 Star Island Rd Montauk NY

$279 nightly

$319 total

Apr 26 - Apr 27

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.

On private beach

Pool

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$187 total

Apr 30 - May 1

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

Sag Harbor Inn

45 West Water Street Sag Harbor NY

$225 nightly

$257 total

Apr 29 - Apr 30

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage storage are also provided.

Pool

Breakfast included

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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?

$545 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.