Title: Shelter Island Heights Vacation Packages & Trips 2026 from CA $706 | Expedia.ca

[Hotels in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Hotels.d183716.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island Heights](https://expedia.ca/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)[Things to do in Shelter Island Heights](https://expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)[Shelter Island Heights Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)

![](https://images.trvl-media.com/place/157359/8df1734b-1204-4cc5-a5a0-67f90d8a76a3.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Shelter Island Heights Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

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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](https://www.expedia.ca/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Railroad Museum of Long Island](https://www.expedia.ca/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) and [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction) 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.

## Top Shelter Island Heights Vacation Deals

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

![Hotel Alameda Highline](https://images.trvl-media.com/lodging/5000000/4340000/4339600/4339531/165c4fb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Alameda Highline

Manhattan

CA $706

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

7.6/10 Good! (793 reviews)

No frills but good location and meets all the needs.

Reviewed on Jan 4, 2026

![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Topping Rose House

CA $839

per person

Mar 12 - Mar 15

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (136 reviews)

Great rooms, staff and food

Reviewed on Sep 28, 2025

![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/8c07d74e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza New York Times Square

Manhattan

CA $1,000

per person

Apr 10 - Apr 13

found 7 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9/10 Wonderful! (2,790 reviews)

Room bathroom the door

Reviewed on Jan 14, 2026

![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### INNSiDE by Meliá New York Nomad

Manhattan

CA $898

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (2,008 reviews)

Check in was quick, amenities were wonderful, staff was very friendly and helpful!

Reviewed on Jan 12, 2026

![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $878

per person

Apr 10 - Apr 13

found 7 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.2/10 Wonderful! (3,348 reviews)

The beds are exceptionally comfortable and clean, and the breakfast offers delightful variety. The friendly staff ensures a welcoming atmosphere. I highly recommend Riu Plaza in Manhattan for a wonderful stay.

Reviewed on Jan 13, 2026

## 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 2 kilometres from the downtown area.

## Things You Should Know About Shelter Island Heights

- Check into one of our [Shelter Island Heights beach hotels](https://www.expedia.ca/d183716-tBeachHotel.Travel-Guide-Filter-Hotels?lang=en&rfrr=ATG.LP.BodyContent) 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 travellers planning a stay in Shelter Island Heights. Consider [Shelter Island House](https://www.expedia.ca/Shelter-Island-Heights-Hotels-Shelter-Island-House.h14997595.Hotel-Information) and [The Chequit](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information).
- 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](null) 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.

## Ready to book your vacation to Shelter Island Heights?

Choose your dates

## Shelter Island Heights Hotel Deals

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $375

CA $514 total

Feb 8 - Feb 9

includes taxes & fees

8.2/10 Very Good! (712 reviews)

The Spa was Amazing! I didn't have breakfast.

Reviewed on Jan 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true&regionId=183716)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Fully refundableReserve now, pay when you stay

CA $288

CA $355 total

Feb 9 - Feb 10

includes taxes & fees

8.8/10 Excellent! (1,005 reviews)

Great place!

Reviewed on Dec 31, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true&regionId=183716)

![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

9.2/10 Wonderful! (187 reviews)

I always have a 5/5 stay at Montauk Blue.

Reviewed on Nov 19, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=28%2F01%2F2026&endDate=29%2F01%2F2026&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true&regionId=183716)

[](https://expedia.ca/Hotel-Search?startDate=28%2F01%2F2026&endDate=29%2F01%2F2026&selected=105612509&PinnedHotelID=105612509&HadPinnedHotel=true&regionId=183716)

[See all 4,705 properties in Shelter Island Heights](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F01%2F2026&endDate=16%2F01%2F2026&regionId=183716)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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- [Sag Harbor Vacations ](https://www.expedia.ca/Sag-Harbor.d154327.Destination-Travel-Guides)
- [Shadmoor State Park ](https://www.expedia.ca/Shadmoor-State-Park-Montauk.d6327477.Vacation-Attraction)
- [Visit Shelter Island ](https://www.expedia.ca/Shelter-Island.dx157359)
- [Shinnecock Nation Cultural Center and Museum ](https://www.expedia.ca/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction)
- [Southampton Arts Center ](https://www.expedia.ca/Southampton-Arts-Center-Southampton.d553248629501562732.Vacation-Attraction)
- [Southampton Vacations ](https://www.expedia.ca/Southampton.d6782.Destination-Travel-Guides)
- [Suffolk County Vacations ](https://www.expedia.ca/Suffolk-County.d553248635083916458.Destination-Travel-Guides)
- [Wolffer Estates Vineyard ](https://www.expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Shelter Island ](https://www.expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)

- [Shelter Island Vacation Rentals ](https://www.expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Shelter Island ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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