Search Hotels in Shorewood, Shelter Island

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20 Dec - 21 Dec
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21 Dec - 22 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Shorewood hotels

Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
29.8 km from Shorewood
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is 2.052.570 ₫
2.360.456 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Clinton Motel
Exterior
Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
29 km from Shorewood
6.4 out of 10, (228)
"Would stay again. "
United States
pamela
The price is 1.710.475 ₫
1.967.046 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Lamplighter Motel - Clinton, Connecticut
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
30.3 km from Shorewood
7.8 out of 10, Good, (1001)
"The staff was friendly. The room was good. "
United States
Narida
The price is 2.661.762 ₫
3.061.026 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Old Saybrook - Westbrook
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
25 km from Shorewood
7.2 out of 10, Good, (69)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Beach nearby
The Huntting Inn

The Huntting Inn

The Huntting Inn
3.5 star property
15.2 km from Shorewood
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is 10.065.488 ₫
11.762.806 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Huntting Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
23.3 km from Shorewood
9.8 out of 10, Exceptional, (60)
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages
Bar (on property)
The Hampton Maid

The Hampton Maid

The Hampton Maid
2.5 star property
23 km from Shorewood
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is 7.460.302 ₫
8.523.395 ₫ total
includes taxes & fees
26 Dec - 27 Dec
The Hampton Maid
Front of property – evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
15 km from Shorewood
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is 7.897.200 ₫
9.924.938 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Mill House Inn
View from property
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
16.5 km from Shorewood
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Bar (on property)
Water's Edge Resort & Spa

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
27.6 km from Shorewood
8.8 out of 10, Excellent, (1002)
"Holiday family tradition!"
United States
Donald
The price is 4.791.795 ₫
5.964.498 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Water's Edge Resort & Spa
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
26.3 km from Shorewood
9.6 out of 10, Exceptional, (1001)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is 8.131.335 ₫
10.008.910 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Saybrook Point Resort & Marina
Individually decorated, individually furnished, desk, laptop workspace
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
27.5 km from Shorewood
7.2 out of 10, Good, (461)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveller
The price is 1.763.894 ₫
2.028.478 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
2 restaurants, American cuisine
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
15.1 km from Shorewood
9.8 out of 10, Exceptional, (161)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is 7.269.519 ₫
9.937.860 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The 1770 House Restaurant & Inn
Private kitchen
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
23.1 km from Shorewood
10.0 out of 10, Exceptional, (1)
The price is 52.498.425 ₫
63.578.289 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Canoe Place Waterfront Residences
Aerial view
East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
14 km from Shorewood
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is 10.344.163 ₫
11.818.066 ₫ total
includes taxes & fees
23 Dec - 24 Dec
East Hampton Art House Bed & Breakfast
Property entrance
The Maidstone

The Maidstone

The Maidstone
4.0 star property
15.2 km from Shorewood
8.0 out of 10, Very good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is 6.598.486 ₫
7.538.770 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Maidstone
Reception
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
20.6 km from Shorewood
9.6 out of 10, Exceptional, (400)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 3.292.679 ₫
3.788.202 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
28.3 km from Shorewood
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
Lobby lounge
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
6.7 km from Shorewood
8.8 out of 10, Excellent, (548)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.528.841 ₫
5.319.557 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Harbor Front Inn
Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
9.7 km from Shorewood
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
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.
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Where to stay in Shorewood

Find the best Shorewood areas for the activities you enjoy most.

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.

Coecles Harbor

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

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.

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.

Top Shorewood Hotel Reviews

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"Loved the 2 bar options on the property."
Jennifer 1-night trip
Posted 2 months ago
Hampton Bays Hotel on Main

Frequently asked questions

What's it like in Shorewood?
You'll be sure to have fun exploring Shelter Island's Shorewood neighbourhood. Consider a visit to Wades Beach as part of your Shorewood travel plans.
How many hotels can I expect to find in Shorewood?
When you want to find places to stay in Shelter Island, start by booking one of Expedia's 7 hotels and other accommodation options in Shorewood.
If I need to cancel my hotel reservation in Shorewood, will I receive a refund?
Yes! The majority of hotel bookings are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Put your dates in and click on "Search", then use the "fully refundable" filter to review the best deals available in Shorewood.
What is there to do in this Shelter Island neighbourhood?
Wades Beach is an attraction you might want to check out while you're in Shorewood. While you're out sightseeing, Shell Beach and Mashomack Preserve are a couple of additional sights to visit in Shelter Island.