Shelter Island Vacation Packages 2025 from $549

Shelter Island flight + hotel vacation packages

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

Ace Hotel New York

Manhattan

Save 100% on your flight

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 coffee shops/cafes and a 24-hour gym. Enjoy a meal from the restaurant and perks like free WiFi. A bar/lounge, a 24-hour front desk, and express check-out are also provided.

1 Hotel Brooklyn Bridge

per person

Sep 8 - Sep 14

found 16 hours 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.

The Benjamin Royal Sonesta New York

Manhattan

Save 100% on your flight

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa and a 24-hour gym are featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A terrace, a snack bar/deli, and dry cleaning are also on offer.

Harpoon House

Save 100% on your flight

per person

Aug 24 - Aug 27

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to New York (JFK)

This bed & breakfast features a restaurant and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.

The Fifty Sonesta Hotel New York

Manhattan

Save 100% on your flight

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A 24-hour gym, valet parking, and laundry facilities are featured at this hotel. Traveling on business? Take advantage of the business center and WiFi in public areas. A snack bar/deli, a lobby fireplace, and express check-in are also on offer.

Top Shelter Island hotels deals

Montauk Yacht Club

32 Star Island Rd, Montauk, NY

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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.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT

Free Cancellation

Reserve now, pay when you stay

Get rates

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.

Montauk Blue Hotel

108 South Emerson Avenue, Montauk, NY

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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

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY

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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

Baron's Cove

31 West Water Street, Sag Harbor, NY

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This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free valet parking and free WiFi. Free self parking, a business center, and a coffee shop are also offered.

Marram

21 Oceanview Terrace, Montauk, NY

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A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage are also on offer.

Pool

Parking included

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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.

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.

Frequently asked questions

How much are vacation packages to Shelter Island?

$549 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.