Hotels in Shorewood, Shelter Island from CA $173

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May 14 - May 15
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May 15 - May 16
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May 17 - May 19
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Shorewood hotels and places to stay

Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Everything was exquisite! "
The price is CA $408
CA $512 total
includes taxes & fees
May 19 - May 20
The Pridwin Hotel
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages
4.0 star property
10.0 out of 10, Exceptional, (26)
"Absolutely the nicest hotel in the area. "
The price is CA $683
CA $818 total
includes taxes & fees
May 22 - May 23
Canoe Place Inn and Cottages
Exterior
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
10.0 out of 10, Exceptional, (1)
"Friends and I stayed the weekend at this rental and loved it! We cooked, watched a movie, played board games, and enjoyed the fall weather. It is in a quiet neighborhood that is an easy drive to town, beaches, and nature preserves. Lisa is a very responsive and gracious host! Would definitely recommend!"
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
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Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (53)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is CA $1,040
CA $1,187 total
includes taxes & fees
May 16 - May 17
East Hampton Art House Bed & Breakfast
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett
4.5 star property
9.8 out of 10, Exceptional, (75)
"The best hotel in the Hamptons! Luxury hospitality without pretension. Quiet, simple and the only one worth the price tag. You will pay the same if not more at any other local hotel and receive the worst service. It would be so easy for Roundtree to just rely on the high summer months to make money and rob you because they can, but they don't. The whole team works with an integrity uncommon to the area. Easy walk to everything in town and while they don't have a restaurant or bar they make up...
The price is CA $812
CA $973 total
includes taxes & fees
May 19 - May 20
The Roundtree, Amagansett
Property grounds
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (422)
"I stay here often. Reliable and consistent hotel. Rooms are spotless. Perfect for single or retired traveler. It’s quiet and attracts a middle aged crowd. Walking distance to town. I’ve never had an issue."
The price is CA $319
CA $365 total
includes taxes & fees
May 20 - May 21
Sag Harbor Inn
Aerial view
Colonial Shores Resort
2.5 star property
9.4 out of 10, Exceptional, (81)
"This is our second 8 day stay. Here for work (Hanging Wallpaper) we really enjoyed our time here. Around the corner from everything. "
The price is CA $341
CA $390 total
includes taxes & fees
May 19 - May 20
Colonial Shores Resort
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (63)
"543y"
The price is CA $377
CA $430 total
includes taxes & fees
May 20 - May 21
House on Chase Creek
Property entrance
Southampton Village Motel
2.5 star property
9.2 out of 10, Wonderful, (42)
"My room was unacceptable, there was mold and the shower was flooding the bathroom all the time, the wifi did not work very well and the owner/manager was not helpful. I had to call every time we needed more towels and she was not welcoming or friendly at all. When we told her about the shower she did not show any remorse"
The price is CA $545
CA $622 total
includes taxes & fees
May 19 - May 20
Southampton Village Motel
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Children's activities
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (234)
"The bathroom was very clean with nice plush towels. The room was also very clean with a comfortable bed. I would definitely recommend this Inn to my friends and relatives. Great location as well!"
The price is CA $173
CA $197 total
includes taxes & fees
May 28 - May 29
Hampton's Vacation Inn
Property grounds
Hampton Maid Motel
2.5 star property
9.0 out of 10, Wonderful, (522)
"The property is well kept and beautiful. I will definitely come back. "
The price is CA $276
CA $316 total
includes taxes & fees
May 16 - May 17
Hampton Maid Motel
1 bedroom, WiFi, bed sheets
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
Outdoor spa tub
The Drake Inn
2.0 star property
9.0 out of 10, Wonderful, (77)
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
The Drake Inn
Deluxe Studio | Living area
East Hampton House Resort
3.0 star property
8.8 out of 10, Excellent, (227)
"Very convenient with own entrance and back deck and parking right in front!! Can walk to dining and breakfast options or make in your own kitchen nook!! "
The price is CA $430
CA $521 total
includes taxes & fees
May 16 - May 17
East Hampton House Resort
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (88)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is CA $399
CA $501 total
includes taxes & fees
May 28 - May 29
Journey East Hampton
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (50)
"Excellent facility and excellent service. Highly recommend. "
The price is CA $614
CA $771 total
includes taxes & fees
May 19 - May 20
Mill House Inn
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (92)
"Looks like the were in the process of updating? Lots of construction people and debris but we also went during off season so it made sense. Have to drive everywhere but still convenient!! "
The Wainscott Inn
Seasonal outdoor pool, open 8:00 AM to 8:30 PM, free cabanas
Bayview Resort
2.5 star property
8.6 out of 10, Excellent, (372)
"The view of the bay is incredible ( I was on 2nd floor) but the structure itself needs some t l c, fresh paint, more tables in room, etc. "
The price is CA $200
CA $237 total
includes taxes & fees
May 20 - May 21
Bayview Resort
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Frequently asked questions

What's it like in Shorewood?

You'll be sure to have fun visiting Shelter Island's Shorewood neighborhood. Consider a visit to Wades Beach as part of your Shorewood travel plans.

What's the best accommodation in Shorewood?

For your stay in Shorewood, Most private house with pool with ocean view is one of the top choices based on our traveler data.

How many hotels will I be able to find in Shorewood?

When you want to find places to stay in Shelter Island, start by booking one of Expedia's 6 hotels and other accommodations in Shorewood.

If I need to cancel my hotel reservation in Shorewood, will I receive a refund?

Yes, you'll find most hotel reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, you may still be able to cancel and receive a refund within a 24-hour period of booking. Add your dates and click on "Search", then filter by "fully refundable" to get the best options available in Shorewood.

Where can I learn more about changing or cancelling my trip to Shorewood?

For more information about picking new dates or cancelling your trip to Shorewood, head over to our customer service page.

What is there to do in this Shelter Island neighborhood?

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.