Shorewood Travel Guide

Shelter Island

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

฿5,740
per adult
Sunday Brunch Sail in Greenport
Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery

฿6,494
per adult
Private Luxury Wine Tours of Long Island Pindar Winery
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

Half Day(PM) North Fork Private Wine & Food Tour by Local Expert

฿14,398
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
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 ฿2,697 per night from 21 Sept to 22 Sept
฿2,697
฿3,101 total
21 Sept - 22 Sept
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. ...
8/10 Very good! (1,009 reviews)
"Room need complete makeover"

Reviewed on 15 Sept 2026

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
The price is ฿15,070 per night from 12 Oct to 13 Oct
฿15,070
฿20,660 total
12 Oct - 13 Oct
includes taxes & fees
Stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Popular attractions Hither Woods Preserve and Hither Hills ...
8.2/10 Very good! (854 reviews)
"Absolutely gorgeous stay!"

Reviewed on 13 Sept 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ฿8,823 per night from 1 Oct to 2 Oct
฿8,823
฿11,028 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.4/10 Very good! (726 reviews)
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."

Reviewed on 15 Sept 2026

Sound View Greenport
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is ฿5,953 per night from 7 Oct to 8 Oct
฿5,953
฿7,419 total
7 Oct - 8 Oct
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,002 reviews)
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."

Reviewed on 12 Sept 2026

Water's Edge Resort & Spa
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is ฿3,960 per night from 1 Oct to 2 Oct
฿3,960
฿5,355 total
1 Oct - 2 Oct
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
The Atlantic Hotel
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is ฿5,604 per night from 23 Sept to 24 Sept
฿5,604
฿6,403 total
23 Sept - 24 Sept
includes taxes & fees
Stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing Company ...
9.2/10 Wonderful! (402 reviews)
"My Husband Phil & I had the Best Stay. Very Quaint Hotel, just a couple of blocks from waterfront.Absolutely spotless, so many sitting areas, Coffee, tea water and ice available 24-7. Our room was spotless, decorated so well. We also had a balcony. James and all staff were so Pleasant and so accommodating. ..."

Reviewed on 14 Sept 2026

Zey Hotel
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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.

Where to stay in Shorewood

Find the best Shorewood areas for the activities you enjoy most.
A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

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

A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

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

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

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.

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 Shelter Island Historical Society.

Shorewood Travel Guide