Shorewood Vacations from $658

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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.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,370 reviews)
Awesome! Close to everything.

Reviewed on Jul 30, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Overpriced and overhyped. Looks like a motel, view is nice but not worth almost 600$

Reviewed on Jul 28, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
I had a wonderful experience. The staff was exceptionally welcoming and helpful throughout my stay, making the visit even more enjoyable. The views were absolutely stunning and added a special touch to the overall atmosphere. I would highly recommend this place to anyone looking for a memorable and relaxing stay. Great and memorable way to celebrate my wife and I wedding anniversary!

Reviewed on Jul 28, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 7
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul 22, 2025

YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Miami (MIA) to Newburgh (SWF)
8.2/10 Very Good! (454 reviews)
solid 3 stars. place was empty, steam room broken, but still had nice time. not worth $350 but worth $250

Reviewed on Jun 1, 2025

Where to stay in Shorewood

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

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach.

Find hotels in Menantic Creek

Shorewood Hotel Deals

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
$111 nightly
The price is $127 total per night from Aug 6 to Aug 7
$127 total
Aug 6 - Aug 7
Total includes taxes and fees
7.6/10 Good! (1,015 reviews)
"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which ..."

Reviewed on Jul 27, 2025

Quality Inn Old Saybrook - Westbrook
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
$1,090 nightly
The price is $1,245 total per night from Aug 27 to Aug 28
$1,245 total
Aug 27 - Aug 28
Total includes taxes and fees
8.2/10 Very Good! (648 reviews)
"I love it"

Reviewed on Jul 22, 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
$80 nightly
The price is $93 total per night from Aug 5 to Aug 6
$93 total
Aug 5 - Aug 6
Total includes taxes and fees
7.6/10 Good! (1,005 reviews)
"The property was clean."

Reviewed on Jul 26, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,058 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

$159
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

$137
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
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.