Shelter Island Vacation Packages 2025/2026 from $394

Shelter Island flight + hotel vacation packages

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

The Inn At Fox Hollow Hotel

Save 100% on your flight

$394

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

1 Hotel Brooklyn Bridge

$1,428

per person

Dec 17 - Dec 21

found 2 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

The Asbury Hotel

Save 100% on your flight

$676

per person

Oct 30 - Nov 5

found 5 hours ago

Roundtrip flight included

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

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.

Park Lane New York

Manhattan

Save 100% on your flight

$1,155

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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.

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$792

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$97 total

Oct 9 - Oct 10

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

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

$527 nightly

$603 total

Oct 1 - Oct 2

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

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Oct 13 - Oct 14

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.

Pool

Breakfast included

Montauk Blue Hotel

108 South Emerson Avenue, Montauk, NY

$149 nightly

$170 total

Oct 26 - Oct 27

Total with taxes and fees

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

Sound View Greenport

58775 County Rd 48, Greenport, NY

$268 nightly

$306 total

Oct 26 - Oct 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 Atlantic Hotel

1655 County Road 39, Southampton, NY

$191 nightly

$218 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, free newspapers, and barbecue grills are also on offer.

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.

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

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.

Frequently asked questions

How much are vacation packages to Shelter Island?

$394 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.