Shelter Island Heights Vacations from $440

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Your Shelter Island Heights Vacation

The easiest way to experience this interesting city is with a customized Shelter Island Heights vacation package. Base yourself in the neighborhood of Orient Point, which is good for views, fishing and nature or go someplace else — our package deals are all about you. Make your trip to Shelter Island Heights even more fulfilling by going sightseeing. 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery are some of the top attractions you'll want to explore. Browse Expedia's wide range of travel options and book your ultimate vacation to Shelter Island Heights today.

The Latest Shelter Island Heights vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $866, price is now $440 per person
$440
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,761, price is now $970 per person
$970
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,306 reviews)
Grace is the best housekeeping attendant!

Reviewed on Oct 11, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,731, price is now $962 per person
$962
per person
Dec 22 - Dec 27
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
The staff go out of their way to make you feel at home

Reviewed on Oct 11, 2025

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,117, price is now $624 per person
$624
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (4,712 reviews)
The Hotel is located in a great location. However, waiting in line for over an hour to check in was less than pleasant. This was a daily occurrence. Additionally, the hotel is VERY dated. The rooms need a MAJOR upgrade especially for the prices. This hotel is a great representation of poor management. Would not reccommend or stay again until the issues were addressed.

Reviewed on Oct 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,847, price is now $1,600 per person
$1,600
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

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Discover the most popular places to visit in Shelter Island Heights

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

What to do in Shelter Island Heights

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

$139
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

$148
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Shelter Island Heights

Shelter Island Heights Hotel Deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road, Shelter Island Heights, NY
$384 nightly
The price is $439 total per night from Oct 19 to Oct 20
$439 total
Oct 19 - Oct 20
Total with taxes and fees
9.4/10 Exceptional! (80 reviews)
"The staff was amazing"

Reviewed on Oct 6, 2025

The Pridwin Hotel
The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
$268 nightly
The price is $307 total per night from Nov 3 to Nov 4
$307 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (36 reviews)
"Always a sold stay on Shelter Island"

Reviewed on Aug 23, 2025

The Chequit
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $98 total per night from Oct 26 to Oct 27
$98 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

Reviewed on Oct 11, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,748 properties in Shelter Island Heights
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.

Shelter Island Heights Beach Vacation

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights vacation. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights vacation packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 1 mile from the downtown area.

Things You Should Know About Shelter Island Heights

  • Check into one of our Shelter Island Heights beach hotels to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door.
  • Alternatively, check out our range of private vacation homes. They're popular with travelers planning a stay in Shelter Island Heights. Consider Shelter Island House and The Chequit.
  • There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our Shelter Island Heights things to do page will let you in on the best of what this place has to offer.
  • Land great deals with a Shelter Island Heights vacation package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start.

Shelter Island Heights Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
40ºF
Max Temp Summer
75ºF
Top Sights
Wolffer Estates Vineyard, 67 Steps Beach and Kontokosta Winery

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Frequently asked questions

How much does a Shelter Island Heights vacation package cost?
You'll find cheap prices from $440 on Expedia for your Shelter Island Heights getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Shelter Island Heights costs.
What are the cheapest months to go to Shelter Island Heights?
April, November and December are the best times to search for cheap Shelter Island Heights vacation packages. Traveling in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Shelter Island Heights?
With around 2 days, you'll have plenty of time to visit popular neighborhoods such as The Heights and Greenport West during your Shelter Island Heights vacation. Make sure to also add Sunset Beach and Shelter Island Country Club to your must-see list. Up for some more adventures? Consider exploring outside of Shelter Island Heights on tours and day trips.
Is it worth booking a vacation package to Shelter Island Heights?
Shelter Island Heights offers everything you need for an unforgettable escape. Begin your Shelter Island Heights vacation on a high note by visiting top attractions like Crescent Beach.
How to find the best Shelter Island Heights package deals?
Use Expedia's handy filters to help you find some of the best Shelter Island Heights package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Shelter Island Heights package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Shelter Island Heights vacation as a package?
You can enjoy significant savings on your Shelter Island Heights escape by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Shelter Island Heights?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Shelter Island Heights break.
How to plan a trip to Shelter Island Heights?

  1. Choose when to go: Check your diary and get packing. Your favorite time of year and the type of activities available will also help you decide when to visit Shelter Island Heights.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Shelter Island Heights.
  3. Explore Shelter Island Heights using our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Shelter Island Heights. You can also save your must-visit places, collaborate with your group and manage all your plans in one place.
  4. Decide how long to go away for: Now that you're up to speed on Shelter Island Heights, you can figure out the perfect length of your break. Put together a draft plan and give yourself enough time for all the things you want to do.
  5. Combine your accommodations and airfare: After you've nailed down your dates and duration, lock in the right Shelter Island Heights vacation package for you.
  6. Add on excursions and experiences: Have a look at our travel guide to find some awesome things to do in Shelter Island Heights in Shelter Island Heights. Book tickets or make reservations as soon as you can to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Shelter Island Heights vacation packages?
Secure your dream trip to Shelter Island Heights with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.