Shorewood Holidays

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Our guide on where to stay in Shorewood

Find the best Shorewood areas and neighborhoods for the activities you enjoy most. Learn more about Shorewood
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.

Find hotels in Silver Beach

Our pick of the best Shorewood Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is NZ$1,101 per night from 19 May to 20 May
NZ$1,101
19 May - 20 May
includes taxes & fees
8.4/10 Very Good! (766 reviews)
Everything was great…

Reviewed on 4 May 2026

Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is NZ$158 per night from 6 May to 7 May
NZ$158
6 May - 7 May
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Parking was easy. Bed mattress terrible. Tired room and furnishings. Basic supplies.

Reviewed on 28 Apr 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$719 per night from 11 May to 12 May
NZ$719
11 May - 12 May
includes taxes & fees
8.4/10 Very Good! (643 reviews)
Clean rooms, great continental breakfast. Was upgraded to waterfront room!!

Reviewed on 3 May 2026

Sound View Greenport
See all 4,125 properties in Shorewood
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.

Frequently asked questions

How much does a Shorewood holiday package cost?
Chart your own course with our Shorewood holiday packages, which start from just . Handpick the flights and hotels that suit your travel plans. Then, add on one or two enriching experiences to round off your unique getaway.
How do I get a cheap travel package to Shorewood?
Creating your own Shorewood holiday package with Expedia is a great way to save. We have more than 550 partner airlines and 1 000 000 properties around the world. With such a fabulous range to choose from, you'll have no difficulty putting together your perfect trip.
Where should I stay in Shorewood?
With fascinating attractions such as Gardiners Bay Country Club and Shell Beach in this neighbourhood, look for a hotel positioned near either one. Shelter Island Historical Society is another Shorewood sight that draws in the crowds.
How far in advance should I book my Shorewood holiday?
It's tricky picking the ideal time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't stress. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Shorewood travel package include?
From hotels and flights to car rentals, Expedia can help you craft a Shorewood package that's right for you. Holidaying for a week or two? Consider a flight, rental car and hotel bundle. If your break is short, a flight and hotel deal may be more your style. Tours and activities can be added once you've made your booking. Our packages make it simple to save and plan.
What should I know before booking a Shorewood travel package?
Whether it's relaxation or adventure you're craving, a Shorewood holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Shorewood Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to pick from worldwide. With so many choices, finding the perfect carrier to whisk you off to Shorewood will be easy.
If I'm not able to travel, can I cancel my Shorewood holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or change your Shorewood holiday package for free if you've booked in the last 24 hours. For older bookings, you can still cancel and rebook, but your car rental company, hotel or airline may impose a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Shorewood

Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

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