Shelter Island Vacation Packages 2026 from $385

Shelter Island flight + hotel vacation packages

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

Arthouse Hotel New York City

Manhattan

Save 100% on your flight

$385

per person

Aug 6 - Aug 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Business travelers can take advantage of the 24-hour business center. Self parking, a library, and a computer station are also offered.

Night Hotel Broadway

Manhattan

Save 100% on your flight

$428

per person

Aug 8 - Aug 12

found 1 day ago

Roundtrip flight included

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

A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Placemakr Wall Street

Manhattan

Save 100% on your flight

$874

per person

Sep 10 - Sep 15

found 1 day ago

Roundtrip flight included

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

This aparthotel features 2 coffee shops/cafes and a gym. Enjoy the a rooftop terrace and perks like free WiFi. A restaurant, a 24-hour front desk, and a communal living room are also provided.

2 bedroom luxury Empire State VIEW

Manhattan

$2,161

per person

Aug 9 - Aug 14

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

OYO Times Square

Manhattan

Save 100% on your flight

$774

per person

Sep 10 - Sep 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features a restaurant, free WiFi in public areas, and express check-out. Dry cleaning, luggage storage, and laundry facilities are also on offer.

Top Shelter Island hotels deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$1,099 nightly

$1,256 total

Jul 7 - Jul 8

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.

Offshore Montauk

71 S Emerson Ave Montauk NY

$618 nightly

$706 total

Jul 1 - Jul 2

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. Express check-out and luggage storage are also provided.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$117 total

Jul 6 - Jul 7

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 is also provided.

Sound View Greenport

58775 County Rd 48 Greenport NY

$496 nightly

$567 total

Jul 14 - Jul 15

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.

Montauk Manor

236 Edgemere St. Montauk NY

$439 nightly

$502 total

Jul 1 - Jul 2

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.

Ocean Surf Resort

84 South Emerson Avenue Montauk NY

$455 nightly

$520 total

Jul 5 - Jul 6

Total with taxes and fees

A seasonal outdoor pool, self parking, and concierge services are featured at this motel. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on offer.

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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

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

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.

A close-up of a beach with various shells and pebbles.

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.

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?

$385 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.