Shelter Island Vacation Packages 2026 from $315

Shelter Island flight + hotel vacation packages

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

INNSiDE by Meliá New York Nomad

Manhattan

$315

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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.

Topping Rose House

Save 100% on your flight

$783

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

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.

1 Hotel Brooklyn Bridge

$1,501

per person

Mar 3 - Mar 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Loews Regency New York Hotel

Manhattan

$1,812

per person

Mar 21 - Mar 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pendry Natirar

Save 100% on your flight

$1,225

per person

Mar 5 - Mar 8

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features 2 restaurants and a seasonal outdoor pool. Family-friendly amenities include a children's club and babysitting. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$418 nightly

$478 total

Jan 25 - Jan 26, 2026

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

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$281 total

Jan 4 - Jan 5, 2026

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. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.

Pool

Hot Tub

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$81 total

Dec 30 - Dec 31

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.

Pet friendly

Parking included

Offshore Montauk

71 S Emerson Ave Montauk NY

$166 nightly

$190 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.

Pool

Pet friendly

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$144 total

Jan 4 - Jan 5, 2026

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Shelter Island?

$315 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.