Shelter Island Vacation Packages 2026 from $544

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

$544

per person

Jul 17 - Jul 20

found 1 day 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

$1,374

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.

2 bedroom luxury Empire State VIEW

Manhattan

$1,288

per person

Jun 16 - Jun 18

just found

Roundtrip flight included

Dallas (DFW) to New York (JFK)

The Towers at Lotte New York Palace

Manhattan

$2,236

per person

Jul 5 - Jul 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

New York Marriott Marquis

Manhattan

Save 100% on your flight

$1,055

per person

Jul 3 - Jul 6

found 21 hours ago

Roundtrip flight included

Dallas (DAL) to New York (JFK)

This luxury hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and a computer station are also on offer.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$633 nightly

$724 total

Apr 29 - Apr 30

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

May 12 - May 13

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

Montauk Yacht Club

32 Star Island Rd Montauk NY

$279 nightly

$319 total

Apr 29 - Apr 30

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

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

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

Free Cancellation

$118 nightly

$136 total

May 19 - May 20

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$170 nightly

$194 total

Apr 29 - Apr 30

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.

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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?

$544 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.