Shorewood Travel Guide

Shelter Island

Popular places to visit

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 Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Shelter Island Whale's Tail

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 care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

Shell Beach

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

Shell Beach

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

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

฿4,716
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

฿4,429
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

฿10,802
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
See all activities in Shelter Island

Top hotels in Shorewood

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is ฿2,602 per night from 12 Oct to 13 Oct
฿2,602
฿2,992 total
12 Oct - 13 Oct
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.8/10 Good! (1,005 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."

Reviewed on 4 Oct 2025

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

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
Fully refundableReserve now, pay when you stay
The price is ฿9,866 per night from 30 Oct to 31 Oct
฿9,866
฿13,465 total
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Our guests praise the room service in their reviews. ...
8.2/10 Very Good! (669 reviews)
"wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities"

Reviewed on 29 Sept 2025

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

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is ฿3,041 per night from 2 Nov to 3 Nov
฿3,041
฿3,498 total
2 Nov - 3 Nov
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"

Reviewed on 5 Oct 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is ฿8,061 per night from 20 Oct to 21 Oct
฿8,061
฿10,799 total
20 Oct - 21 Oct
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (577 reviews)
"Nice views on sunset"

Reviewed on 3 Oct 2025

Sound View Greenport
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
Stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
7/10 Good! (948 reviews)
"Really more of a motel not a hotel. Room was basic but adequate and clean. Close to Southampton. They were fully booked on one of the weekend days of our stay so rate that night was high for this type of lodging."

Reviewed on 30 Sept 2025

Get rates
The Atlantic Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is ฿8,448 per night from 6 Nov to 7 Nov
฿8,448
฿10,527 total
6 Nov - 7 Nov
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,005 reviews)
"Relaxing wonderful staff!"

Reviewed on 6 Oct 2025

Saybrook Point Resort & Marina
See all 4,027 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.

Other neighbourhoods around Shorewood

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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Menantic Creek
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Montclair Colony

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

Montclair Colony
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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 Crescent Beach and Sunset Beach.

Silver Beach
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Coecles Harbor

While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Mashomack Preserve are some notable places to visit nearby.

Coecles Harbor
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Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Hay Beach

Shorewood Travel Guide