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

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Our top choices for Shorewood hotels

1. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
4.2 mi from Shorewood
9.0 out of 10, Wonderful, (674 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is £127
includes taxes & fees
19 Nov - 20 Nov
The Harbor Front Inn

2. The Chequit

The Chequit
3.0 star property
2.9 mi from Shorewood
9.0 out of 10, Wonderful, (76 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is £142
includes taxes & fees
22 Nov - 23 Nov
The Chequit

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
4.1 mi from Shorewood
10.0 out of 10, Exceptional, (187 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is £183
includes taxes & fees
1 Dec - 2 Dec
Silver Sands Motel & Beach Bungalows

4. Sound View Greenport

Sound View Greenport
4.0 star property
5 mi from Shorewood
8.4 out of 10, Very good, (764 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is £151
includes taxes & fees
17 Nov - 18 Nov
Sound View Greenport

5. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
4.5 mi from Shorewood
9.4 out of 10, Exceptional, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is £177
includes taxes & fees
4 Nov - 5 Nov
The Shoals Suites and Slips

6. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
3.5 mi from Shorewood
9.4 out of 10, Exceptional, (684 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is £187
includes taxes & fees
4 Nov - 5 Nov
Sag Harbor Inn

7. Zey Hotel

Zey Hotel
3.5 star property
4.3 mi from Shorewood
9.2 out of 10, Wonderful, (443 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is £124
includes taxes & fees
5 Nov - 6 Nov
Zey Hotel

8. House on Chase Creek

House on Chase Creek
2.5 star property
2.7 mi from Shorewood
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is £157
includes taxes & fees
9 Nov - 10 Nov
House on Chase Creek

9. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
3.6 mi from Shorewood
9.0 out of 10, Wonderful, (320 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is £299
includes taxes & fees
17 Nov - 18 Nov
Faraway Sag Harbor

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
4.9 mi from Shorewood
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is £227
includes taxes & fees
15 Nov - 16 Nov
Cliffside Resort Condominiums

11. Oyster Estate

Oyster Estate
4.0 star property
4.2 mi from Shorewood
9.2 out of 10, Wonderful, (301 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is £177
includes taxes & fees
17 Nov - 18 Nov
Oyster Estate

12. American Beech Hotel

American Beech Hotel
3.5 star property
4.3 mi from Shorewood
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is £243
includes taxes & fees
4 Nov - 5 Nov
American Beech Hotel

13. The Menhaden

The Menhaden
3.5 star property
4.2 mi from Shorewood
9.6 out of 10, Exceptional, (195 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is £266
includes taxes & fees
3 Dec - 4 Dec
The Menhaden

14. East Hampton House Resort

East Hampton House Resort
3.0 star property
9.9 mi from Shorewood
9.0 out of 10, Wonderful, (351 reviews)
"the place is great. the location was excellent for the film festival. The room itself was very roomy clean cute little balcony. I will book it again for the festival."
United States
Tina
The price is £143
includes taxes & fees
4 Nov - 5 Nov
East Hampton House Resort

15. North Fork Resort

North Fork Resort
3.0 star property
4.8 mi from Shorewood
9.6 out of 10, Exceptional, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is £265
includes taxes & fees
12 Nov - 13 Nov
North Fork Resort

16. The Sagaponack

The Sagaponack
3.0 star property
7.9 mi from Shorewood
8.8 out of 10, Excellent, (295 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is £219
includes taxes & fees
3 Dec - 4 Dec
The Sagaponack

17. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
12.4 mi from Shorewood
7.2 out of 10, Good, (1,004 reviews)
"Lots of parking, rooms were clean and smelt nice"
United States
miranda
The price is £104
includes taxes & fees
10 Nov - 11 Nov
The Atlantic Hotel

18. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
12.8 mi from Shorewood
9.6 out of 10, Exceptional, (615 reviews)
"great spot to stay,"
United States
Armando
The price is £122
includes taxes & fees
10 Nov - 11 Nov
The Bentley Hotel Southampton

19. Journey East Hampton

Journey East Hampton
4.0 star property
10.3 mi from Shorewood
9.2 out of 10, Wonderful, (210 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
The price is £215
includes taxes & fees
9 Nov - 10 Nov
Journey East Hampton

20. The Maidstone

The Maidstone
4.0 star property
9.4 mi from Shorewood
8.2 out of 10, Very good, (182 reviews)
"lovely hotel - would stay again but would ask for a back room as the noise from the very busy road is constant. Otherwise awesome amenities, loved that you had a ghd hairdryer and straighteners. Every where smelt divine! Breakfast was lovely and a decent coffee."
Australia
Clara
The price is £196
includes taxes & fees
12 Nov - 13 Nov
The Maidstone
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.

Compare popular hotels in Shorewood

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A two-story house with a balcony, outdoor seating area, and a variety of plants.
Zey Hotel
3.5 star property
9.2
Wonderful
443 reviews
View
A satin fabric with lace detailing.
The Harbor Front Inn
3.5 star property
9.0
Wonderful
674 reviews
View
A large, multi-story building with a porch and outdoor seating area, featuring multiple windows and a balcony.
The Chequit
3.0 star property
9.0
Wonderful
76 reviews
View
A beachside outdoor seating area with white Adirondack chairs and a fire pit.
Silver Sands Motel & Beach Bungalows
4.0 star property
10.0
Exceptional
187 reviews
View
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
Sag Harbor Inn
3.5 star property
9.4
Exceptional
684 reviews
View

Where to stay in Shorewood

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

Menantic Creek

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

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 Shell Beach.

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.

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 Shell Beach and Wades Beach.

Top Shorewood Hotel Reviews

Frequently asked questions

When is the best time to go to Shorewood?
The best time to visit Shorewood is during the summer months, from June to August, when the weather is warm and sunny, making it ideal for outdoor activities.

During this period, the average daily temperatures range from 20°C to 28°C, great for enjoying the beaches and water sports on Lake Ontario. The town truly comes alive with various festivals and events, including the popular Shorewood Summer Festival, offering live music, local crafts, and food stalls.

For those who prefer a quieter experience with pleasant weather, late spring (May) and early autumn (September to early October) are also excellent choices. Temperatures are milder, typically between 15°C and 22°C, and the crowds are smaller. This is a great time for couples to enjoy scenic walks along the waterfront or explore the numerous local vineyards without the peak season bustle.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shorewood.
How much is the nightly rate at a Shorewood hotel?
Hotel prices in Shorewood often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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