Deals on vacations and trips to Shelter Island Heights

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Shelter Island Heights flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Free WiFi in public areas, a garden, and a picnic area are available at this bed & breakfast. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.
Ruschmeyers Hotel

Ruschmeyers Hotel

3 out of 5
Save 100% on your flight
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and express check-out are also on offer.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 10
found 1 day 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.
Pestana Park Avenue

Pestana Park Avenue

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug 22 - Aug 27
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a terrace, laundry facilities, and self parking. A safe deposit box is provided and the front desk is staffed around-the-clock.
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 28 - Sep 1
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, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

Top Shelter Island Heights hotels deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road, Shelter Island Heights, NY
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This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.
On private beach
Pool
The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
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This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a coffee shop are also provided.
Pet friendly
Parking included
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
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This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Pet friendly
Parking included
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
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
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
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.
Baron's Cove

Baron's Cove

4 out of 5
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.
Pool
Spa
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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

Sunset Beach

4.5/5(9 reviews)

Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Sunset Beach

Crescent Beach

4.5/5(4 reviews)

Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Crescent Beach

Shelter Island Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

Shelter Island Country Club

Frequently asked questions

How much are vacation packages to Shelter Island Heights?
With Travelocity vacation packages, you can live the high life in Shelter Island Heights for a mere $573. Activities, flights and hotels — we’re a one-stop shop for all of them. You’ll save loads just for bundling together your bookings. And with everything taken care of before you even go, you won’t have to worry about a thing.
How long should my Shelter Island Heights vacation be?
The majority of travelers secure a hotel for 2 nights in Shelter Island Heights. But that doesn’t necessarily mean you have to follow suit. How long you stay all comes down to what you feel like doing on your vacation. If you’d like to explore every part of this incredible place, consider staying another night or so (or even longer!).
Where can I get the best vacation package deals for Shelter Island Heights?
With as many as 400 partner airlines and 1,000,000 hotels around the world, it’s hard to top Travelocity. Make the most of our comprehensive range and create the perfect Shelter Island Heights package deal. Doesn’t it feel amazing when travel is that easy?
Why should I purchase my Shelter Island Heights vacation bundle with Travelocity?
Whether you’re searching for the ultimate unplugged escape or you crave the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to scour through countless websites for the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need anything at all.
Can I save money on my Shelter Island Heights car rental if I bundle it with a hotel or flight?
With a Shelter Island Heights vacation package, you can bundle your car, flight and hotel bookings and save loads. If you’d love to explore the best of this fantastic destination, why not make a beeline for Times Square? This popular attraction is 90 mi from Shelter Island Heights. With your own wheels, you’ll be there in a jiffy.
Which airport is best for Shelter Island Heights?
Bradley Intl. Airport (BDL) is one of the busiest airports in Shelter Island Heights. You’ll find it 60 mi north of the city center. Other options available to you are MacArthur Airport (ISP) (45 mi away from central Shelter Island Heights) and Tweed - New Haven Regional Airport (HVN) (30 mi away from central Shelter Island Heights).
What is there to do in Shelter Island Heights?
Shelter Island Heights has plenty of things to see and do, such as Sunset Beach and Crescent Beach. These two fantastic attractions top most visitors’ to-do lists.
Where should I stay when visiting Shelter Island Heights?
If you’re looking for a place to spend your nights, take a look at the House On Chase Creek. It’s the top choice for many visitors.

Photos of local treasures

Browse Shelter Island Heights vacation photos for more inspiration

Photo by Erisa Dilo
Photo by Erisa Dilo
Photo by tom owens
Photo by tom owens
Photo by tom owens
Photo by tom owens
Photo by Brian V. Rowe
Photo by Brian V. Rowe