Shelter Island Vacation Packages 2025/2026 from $224

Shelter Island flight + hotel vacation packages

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

Windrose On Hudson

$224

per person

Jan 26 - Jan 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and luggage storage are also offered.

INNSiDE by Meliá New York Nomad

Manhattan

$334

per person

Jan 23 - Jan 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

Radio Hotel

Manhattan

$264

per person

Jan 21 - Jan 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Ink 48 Hotel

Manhattan

Save 100% on your flight

$344

per person

Jan 23 - Jan 28

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 express check-out and WiFi in public areas. Dry cleaning, luggage storage, and wedding services are also on offer.

Hilton Garden Inn Westchester Dobbs Ferry, NY

$230

per person

Jan 30 - Feb 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a snack bar/deli, and a grocery/convenience store are also offered.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$308 nightly

$351 total

Dec 10 - Dec 11

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 Blue Hotel

108 South Emerson Avenue Montauk NY

Get rates

This hotel features an indoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.

Pool

Hot Tub

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$116 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Sound View Greenport

58775 County Rd 48 Greenport NY

$203 nightly

$232 total

Nov 23 - Nov 24

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

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$253 nightly

$291 total

Nov 30 - Dec 1

Total with taxes and fees

A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.

Pool

Hot Tub

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$175 nightly

$202 total

Nov 23 - Nov 24

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.

Popular places to visit

Shelter Island Historical Society

4/5(1 review)

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

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?

$224 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.