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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $734, price is now $419 per person
$419
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Vintedge Residences

Vintedge Residences

2 out of 5
Save 100% on your flight
Price was $1,540, price is now $859 per person
$859
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a terrace, and luggage storage are also offered.
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was $1,723, price is now $992 per person
$992
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a communal living room, and express check-out are also offered.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,259, price is now $740 per person
$740
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
This hotel 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.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $5,317, price is now $3,162 per person
$3,162
per person
Sep 22 - Sep 29
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
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.

Top Shelter Island Heights hotels deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
$686 nightly
The price is $784 total per night
$784 total
Aug 24 - Aug 25
Total with taxes and fees
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
$383 nightly
The price is $437 total per night
$437 total
Aug 13 - Aug 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a coffee shop are also provided.
West Neck Guesthouse

West Neck Guesthouse

3.5 out of 5
31 W Neck Rd Shelter Island Heights NY
$314 nightly
The price is $358 total per night
$358 total
Aug 3 - Aug 4
Total with taxes and fees
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden and a picnic area are also provided.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
$102 nightly
The price is $118 total per night
$118 total
Aug 23 - Aug 24
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.
Pet friendly
Parking included
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$404 nightly
The price is $462 total per night
$462 total
Aug 18 - Aug 19
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 Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
$739 nightly
The price is $844 total per night
$844 total
Aug 30 - Aug 31
Total with taxes and fees
This luxury 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.
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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.

Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 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.
See properties

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 $419. 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

A pebbled beach with a sunset and a distant bridge.
A lake with houses on the shore, surrounded by trees and a clear sky.
A coastal landscape with a sunset, a marina, and a residential area.
A marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
A calm lake reflecting trees and a clear sky.

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