Name: Pier Blue Inn Old Saybrook - Essex
Price range: CA $128
Rating: 8

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.

Top Shelter Island Heights Vacation Deals

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

JW Marriott Essex House New York

Manhattan

CA $1,475

per person

Apr 1 - Apr 5

found 2 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)

8.8/10 Excellent! (1,001 reviews)

Great location - expensive for your return.

Reviewed on Feb 16, 2026

Pendry Natirar

CA $3,138

per person

May 3 - May 9

found 9 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Newark Liberty Intl. Airport (EWR)

9.8/10 Exceptional! (7 reviews)

The staff is lovely and the property gorgeous. The room could have been more complete (no slippers to be found and no in-room mini bar amenities, which was surprising). The grounds are pristine and peaceful.

Reviewed on Jun 13, 2025

1 Hotel Central Park

Manhattan

CA $2,167

per person

May 17 - May 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (1,001 reviews)

Service at the hotel was fantastic!!! Beds are comfy, and bathrooms are very very nice!

Reviewed on Feb 21, 2026

The Fifth Avenue Hotel

Manhattan

CA $1,634

per person

Apr 13 - Apr 16

found 1 hour ago

Roundtrip flight included

Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)

9.6/10 Exceptional! (159 reviews)

EVERYTHIING WAS 👌. 6 stars! Thank you Karla and the wonderful team.

Reviewed on Feb 21, 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 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 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.

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Shelter Island Heights Hotel Deals

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $511

CA $701 total

Mar 4 - Mar 5

includes taxes & fees

8.4/10 Very Good! (735 reviews)

Staff wasn’t friendly, amenities not working, pools were closed, heating system in the room was very loud, made it hard to sleep.

Reviewed on Feb 27, 2026

Montauk Manor

236 Edgemere St. Montauk NY

CA $206

CA $262 total

Mar 30 - Mar 31

includes taxes & fees

9.2/10 Wonderful! (1,299 reviews)

Always such a pleasure at the Manor.

Reviewed on Feb 28, 2026

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Fully refundable

CA $128

CA $148 total

Mar 4 - Mar 5

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Very clean room. Staff was excellent. Very welcoming. Would and will stay there again, no question.

Reviewed on Feb 22, 2026

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.