Shorewood Vacations from $242

Book a Hotel + Flight or Car together to unlock savings

Your Shorewood Vacation

Our Shorewood vacation packages are a fast and convenient way to plan and book your next break. Uncover the magic of this unique neighborhood without the burden of having to plan everything yourself. Your trip to Shorewood wouldn't be complete without a stop at big-name attractions nearby such as Sunset Beach, Gardiners Bay Country Club and Crescent Beach. Stop daydreaming and start doing. When it's time to lock in your ideal vacation to Shorewood, Expedia will help get you there.

The Latest Shorewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $571, price is now $242 per person
$242
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,030 reviews)
The staff were super welcoming, it was a large hotel room on the top floor. Would definitely stay here again!

Reviewed on Oct 30, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $574, price is now $296 per person
$296
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,629, price is now $852 per person
$852
per person
Jan 15 - Jan 18
found 20 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Nice hotel , needs a bit of tender love and care !

Reviewed on Oct 14, 2025

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,584, price is now $845 per person
$845
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.8/10 Exceptional! (58 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $749, price is now $407 per person
$407
per person
Jan 17 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,140 reviews)
Clean room, friendly and helpful staff

Reviewed on Nov 3, 2025

Where to stay in Shorewood

Find the best Shorewood areas and neighborhoods for the activities you enjoy most. Learn more about Shorewood
Default Image

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

Find hotels in Coecles Harbor

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
$354 nightly
The price is $405 total per night from Nov 4 to Nov 5
$405 total
Nov 4 - Nov 5
Total with taxes and fees
8.2/10 Very Good! (680 reviews)
Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely

Reviewed on Oct 26, 2025

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 refundableReserve now, pay when you stay
$80 nightly
The price is $93 total per night from Nov 12 to Nov 13
$93 total
Nov 12 - Nov 13
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Always a great stay at Pier Blue. Comfy bed and plenty of room.

Reviewed on Oct 26, 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Dec 1 to Dec 2
$103 total
Dec 1 - Dec 2
Total with taxes and fees
7.6/10 Good! (1,010 reviews)
It was a nice clean hotel.

Reviewed on Oct 27, 2025

Quality Inn Old Saybrook - Westbrook
See all 4,011 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Shorewood

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

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

Wades Beach

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

Wades Beach

Things to do

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
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

$179
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.