Shorewood Vacations from $491

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul 18, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
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)
The water views of the Sound were spectacular & were accessible for every meal. The staff was friendly & accommodating -- they had lots of good meal recommendations both in house & for outside restaurants. This inn had a very peaceful vibe -- would definitely return!

Reviewed on Jul 22, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Sep 1 - Sep 8
found 1 day 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

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Facilities mediocre. Location and staff excellent.

Reviewed on Jul 19, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul 17, 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 Wades Beach and Shelter Island Historical Society.

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 3 to Aug 4
$127 total
Aug 3 - Aug 4
Total includes taxes and fees
7.6/10 Good! (1,001 reviews)
Swimming pool is the best
"The pool was the best part of the hotel. Warm and deep enough, long enough to actually swim some 1/2 laps"

Reviewed on Jul 14, 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
$1,082 nightly
The price is $1,236 total per night from Jul 30 to Jul 31
$1,236 total
Jul 30 - Jul 31
Total includes taxes and fees
8.2/10 Very Good! (647 reviews)
"the property is beautiful however there was construction being done upon the premises and certain areas were closed off"

Reviewed on Jul 14, 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 Jul 23 to Jul 24
$93 total
Jul 23 - Jul 24
Total includes taxes and fees
7.6/10 Good! (1,001 reviews)
"Very convenient to the beaches and very clean room. I had some trouble with the door lock but nothing major. I'm a doofus. Will definitely return."

Reviewed on Jul 16, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,123 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

Shelter Island Historical Society

4/5(1 review)

You can spend time studying 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

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.