Deals on vacations and trips to Shelter Island Heights

Save when you book Shelter Island Heights package deals

Choose two or more items and save on your trip:

Shelter Island Heights flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
2 bedroom luxury Empire State VIEW

2 bedroom luxury Empire State VIEW

2 out of 5
Manhattan
Price was $2,722, price is now $1,415 per person
$1,415
per person
Jul 10 - Jul 12
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Price was $4,994, price is now $2,698 per person
$2,698
per person
Jul 18 - Jul 25
found 23 hours 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.
Seven Beach Lane

Seven Beach Lane

2 out of 5
Save 100% on your flight
Price was $2,819, price is now $1,588 per person
$1,588
per person
Jul 21 - Jul 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $4,410, price is now $2,705 per person
$2,705
per person
Jul 1 - Jul 4
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
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.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,563, price is now $1,681 per person
$1,681
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
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 Heights hotels deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
$354 nightly
The price is $405 total per night
$405 total
May 28 - May 29
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
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$493 nightly
The price is $563 total per night
$563 total
May 12 - May 13
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
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night
$192 total
May 25 - May 26
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.
Pool
Hot Tub
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
$299 nightly
The price is $341 total per night
$341 total
May 11 - May 12
Total with taxes and fees
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.
On private beach
Pool
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $154 total per night
$154 total
May 17 - May 18
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. 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. There's a garden and multilingual staff can provide around-the-clock assistance.
Pool
Pet friendly
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
$91 nightly
The price is $104 total per night
$104 total
May 17 - May 18
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
Don't see what you're looking for?
See all available properties in Shelter Island Heights
View all properties
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

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

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 $1,415. 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

Sunrise at Orient Point
coastal landscape at Greenport at the islands of shelter islands heights, county New York
his breathtaking drone shot captures the serene beauty of Southold in The Hamptons, New York. As the sun sets, it casts a golden glow over the lush landscapes and the expansive waters of Peconic Bay.
Shelter Island Heights
Shelter Island Heights

Explore More Ways to Travel with Travelocity