Shorewood Holidays

Book a Hotel + Flight or Car together to unlock savings

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 Crescent Beach.

Find hotels in Silver Beach

Top hotels in Shorewood

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 15.271.980 ₫ per night from 30 Apr to 1 May
15.271.980 ₫
20.938.147 ₫ total
30 Apr - 1 May
includes taxes & fees
8.4/10 Very Good! (753 reviews)
WE HAD A LOVELY WEEKEND. SERVICE WAS EXCELLENT.

Reviewed on 6 Apr 2026

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is 6.265.113 ₫ per night from 13 Apr to 14 Apr
6.265.113 ₫
7.659.089 ₫ total
13 Apr - 14 Apr
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
it was our first time and we really enjoyed the place. The Band was amazing! Being at the resort made our weekend great. Will definitely be back!

Reviewed on 11 Apr 2026

Water's Edge Resort & Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is 4.058.017 ₫ per night from 3 May to 4 May
4.058.017 ₫
6.892.588 ₫ total
3 May - 4 May
includes taxes & fees
8.4/10 Very Good! (630 reviews)
The staff was very friendly professional. Very engaging. The room was spotless and nice. it faced the Long Island sound breathtaking view are sliding glass door open up to a patio with steps that lead right to the beach ……. Stunning

Reviewed on 12 Apr 2026

Sound View Greenport
See all 4,089 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 1null000null000 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.

Popular places to visit

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

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve