THE 10 BEST Hotels in Shelter Island 2023
Shelter Island Hotels
and Places to StayEnter dates to find the best prices
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Popular hotels in Shelter Island right now
14 properties in Shelter Island
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Inn
Michael M
@S7329MNmichaelm
Reviewed on Jun 11, 2023
A little R&R.
"The room was spacious and bed very comfortable and bedding was supreme."
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#1 Best Value of 14 places to stay in Shelter Island
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
Lily P
@lilypC7397IB
Reviewed on Jun 19, 2023
Highly highly recommend!!
"We just wrapped up a weekend stay at the house on chase creek and can’t say enough good things about it! We stayed in the Queen room and it was perfect. The value that you get for the price here is incredible - this..."
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#2 Best Value of 14 places to stay in Shelter Island
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Inn
Yeuming Chou
@yeumingchou
Reviewed on Aug 7, 2022
Great service and convenient location
"Love the big comfortable room and service."
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#3 Best Value of 14 places to stay in Shelter Island
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Judy M
@JudyM1040
Reviewed on Aug 12, 2021
Shelter Island House
"Our room was large, immaculate w/ a spacious walk-in shower."
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#4 Best Value of 14 places to stay in Shelter Island
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pandablanco
@pandablanco
Reviewed on Jul 1, 2023
The newly renovated Pridwin did not disappoint
"We booked a water view room which was relaxing and well stocked."
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#5 Best Value of 14 places to stay in Shelter Island
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Tim from NYC
@TimfromNYC
Reviewed on Sep 8, 2021
Relaxing Summer Getaway with Hardworking Service Team
"I have known Ram's Head Inn (RHI) all my life. I was born and raised across the water in Greenport. Since 2000, my husband and I would celebrate special occasions at Ram's Head including our August 2019 Wedding..."
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#6 Best Value of 14 places to stay in Shelter Island
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Harriet W.
@ManhattanEscapist
Reviewed on Sep 16, 2019
Fabulous Weekend
"We are two friends who were looking for a quick escape from New York City without a car. We found more than we could have hoped for in the Dering Harbor Inn. Travel from the city was easy, we took the LIRR and..."
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#7 Best Value of 14 places to stay in Shelter Island
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Small Hotel
KNICKRD
@KNICKRD
Reviewed on Jul 17, 2020
Disappointed, But.....
"I gave it 4 stars only because of the access and use of Shelter Island House.
After our friends booked a room at Shelter Island House for $275, we tried, and it was now $400, we then searched for a more reasonable..."
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#8 Best Value of 14 places to stay in Shelter Island
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Inn
LAM1971
@1971LAM
Reviewed on Oct 12, 2020
Great Price. Needs more B&B
"We stayed two nights with friends of ours. Beautiful little Victorian House on Shelter Island. Bedrooms decent size. All baths private but across hall from bedrooms. Doors between rooms very thin so can hear a lot..."
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#9 Best Value of 14 places to stay in Shelter Island
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Bed and Breakfast
Ashley C
@ashleyelpern
Reviewed on Jul 22, 2019
Excellent location and great accommodations!
"What a lovely place to stay on Shelter Island! My husband and I had a great room at this cozy bed and breakfast. We really were happy to have air conditioning and our own little porch to enjoy the mornings on. The..."
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#10 Best Value of 14 places to stay in Shelter Island
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Bed and Breakfast
abmullins
@abmullins
Reviewed on Aug 14, 2018
Comfortable Weekday Stay
"My friend and I stayed here during mid-week in August. We arrived late in the evening on the 11pm ferry. The house was very easy to find and our names were left on the door of our room. The decor is a bit dated, but..."
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#11 Best Value of 14 places to stay in Shelter Island
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Bed and Breakfast
Angela Houlihan
@Ahoulihan1
Reviewed on Sep 18, 2021
Perfect Setting
"This is a beautiful bed and breakfast in a beautiful setting. Deb and Frank were very welcoming and made us feel at home the entire time!! The room was so comfortable and clean!! Would go back again!!!
Lots to do..."
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#12 Best Value of 14 places to stay in Shelter Island
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BnMadven
@BnMadven
Reviewed on Aug 27, 2018
Scene-y Inconsistence
"During our brief day drip to Shelter Island, my boyfriend wanted to check out Sunset Beach (and so the review is based only on the restaurant/bar and not on the hotel itself). So I made a late lunch reservation at..."
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#13 Best Value of 14 places to stay in Shelter Island
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Bed and Breakfast
kcsch
@kcsch
Reviewed on Nov 3, 2006
Four West Neck Road Bed & Breakfast
"I think the term "Bed & Breakfast" is a bit misguided. This is not a bed and breakfast, it is someone's home and they are charging you to stay. First thing the owners smoke so even though the windows and doors are..."
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#14 Best Value of 14 places to stay in Shelter Island
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Bed and Breakfast
theresa d
@theresad277
Reviewed on Sep 23, 2023
Best of North Fork
"It has an amazing screened in porch and a beautiful breakfast room and library."
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#3 Best Value of 7 places to stay in Greenport
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flossem
@flossem1049
Reviewed on Apr 29, 2023
Another Great Stay!
"Our room was spacious, spotless with a very comfy bed, big bathroom with fluffy towels and a generous sitting area."
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#1 Best Value of 8 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Specialty Hotel
chiragvshah
@chiragvshah
Reviewed on Sep 9, 2021
Great Labor Day Weekend Away to end the summer!
"The property is very nice, clean and was perfect for us, the 2 queen beds room was large enough for the 4 us and the convenience to be able to walk to town was great."
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#1 Best Value of 3 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
luv2travel1332
@luv2travel1332
Reviewed on May 25, 2021
Fantastic stay
"The room was nicely appointed and very comfortable, with lovely water views, and the B&B was in a great location, so easy and pleasant to walk the couple blocks into town."
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#1 Best Value of 7 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Guest house
Jennie U
@jennieuranga
Reviewed on Oct 12, 2021
2 Bedroom Suite
"The room was meticulously clean and up to date."
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#6 Best Value of 7 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Cp Sclafani
@CS52281
Reviewed on Jan 16, 2022
An Amazing Place to Stay
"The room was comfortable and clean."
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#4 Best Value of 8 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Bed and Breakfast
Maggie J
@maggiej663
Reviewed on Oct 25, 2023
Wonderful stay at Tapestry House
"I cannot recommend this Bed and Breakfast enough. It is absolutely gorgeous without being pretentious. Joan welcomed us as if we were her oldest and dearest friends. We had a wonderful relaxing weekend, and..."
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#2 Best Value of 7 places to stay in Greenport
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
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Small Hotel
Sandyw248
@Sandyw248
Reviewed on Sep 30, 2021
Convenient Location in Greenport
"The Gallery Hotel is right on Main Street in the beautiful harbor front town of Greenort- a convenient spot amidst shops, restaurants and waterfront activities. This boutique hotel has a beautiful interior, with..."
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#4 Best Value of 7 places to stay in Greenport
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Motel
Sharon K
@SharonSunnyside
Reviewed on Nov 19, 2023
Roadside-style motel, but perfect and new! With private beach!
"I LOVED this place and will be back next year! They just reopened in July after a brand-new remodel, and everything is perfect---fluffy pillows and towels, gorgeous bathroom with nice soap and cotton robes, a light..."
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#7 Best Value of 8 places to stay in Greenport
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Bed and Breakfast
LloydF1952
@LloydF1952
Reviewed on Aug 27, 2018
Warm and Welcoming
"Wonderful place in Greenport. The owner, Vince went out of his way to make our experience wonderful...it was my wife's birthday and he had a rose and birthday balloon waiting for us. The room was beautifully..."
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#5 Best Value of 7 places to stay in Greenport
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Inn
Ray O
@rayo924
Reviewed on Apr 13, 2023
Great location. Historical homes. Nice
"Water hot and room clean."
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#7 Best Value of 7 places to stay in Greenport
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Motel
Nancy C
@Nancy C
Reviewed on Aug 8, 2017
Perfect for young families at snack bar
"Remember those days as a kid when you spent all day at the beach or playing in the pool and Mom suggested going out for dinner? Drossos snack bar is just the place for families with young kids, or there's, and yes..."
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#8 Best Value of 8 places to stay in Greenport
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Bed and Breakfast
#3 Best Value of 9 places to stay in Southold
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Cabin/Campground
rngrfan4life
@rngrfan4life
Reviewed on Aug 19, 2020
Small campsites
"We camped here with our family the middle of the heat wave. The pool is maximum 15 people and the campsites are very close together. There was no movie when we were there because they were working on the screen..."
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#2 Best Value of 3 places to stay in Greenport
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Andrew Z
@andrewz2023
Reviewed on Jan 2, 2023
Must Visit
"The room was large, beautifully decorated and pristine."
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#2 Best Value of 3 places to stay in Southold
This hotel description was created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for this description. Please read full traveler reviews for more details and information. If you believe something in this AI-generated description is inaccurate, please share your feedback.
Shelter Island Hotels Information
Hotels in Shelter Island | 14 |
|---|---|
Hotels Prices From | $161 |
Hotels Reviews | 1,176 |
Hotels Photos | 1,052 |
Travel high season | Jun - Aug |
Travel low season | Dec - Feb |
High season avg price | $441 |
Low season avg price | $199 |
Not sure when to visit?
Price trends, weather and things to do can help you make a decision.
Season
Avg. price/night
Avg. temperature
Avg. precipitation
Dec - Feb
Avg. price/night
$199
LOWEST
$171$703
Avg. temperature
34ºF
COLDEST
7ºF93ºF
Avg. precipitation
43in
WETTEST
29 in54 in
Mar - May
Avg. price/night
$285
$171$703
Avg. temperature
48ºF
7ºF93ºF
Avg. precipitation
39in
29 in54 in
Jun - Aug
Avg. price/night
$441
HIGHEST
$171$703
Avg. temperature
72ºF
WARMEST
7ºF93ºF
Avg. precipitation
32in
DRIEST
29 in54 in
Sep - Nov
Avg. price/night
$331
$171$703
Avg. temperature
57ºF
7ºF93ºF
Avg. precipitation
42in
29 in54 in
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Shelter Island. Select dates and complete search for nightly totals inclusive of taxes and fees.
Hotels near the sights
Mashomack PreserveThis Nature Conservancy property spans 2,100 acres, and accounts for one-third of the land on Shelter Island.Read more
Shelter Island Historical SocietyThe Havens House was built in 1743 and is now on the State & National Registries of Historic Places. The Museum features rotating exhibits. Our Archival Vault holds over 50,000 maps, deeds, diaries, letters, photos, and other historical documents. These are available for viewing by appointment. Admission is free. Donations accepted.Read more
Sylvester Manor Educational FarmVisitors are welcome to walk the grounds and trails, visit the farmstand, enjoy one of our many arts, music and educational programs and take a tour of the historic Manor House during scheduled tour dates. Our mission is to cultivate, preserve, and share these lands, buildings, and stories- inviting new thought about the importance of food, culture and place in our daily lives. Once a Native American hunting and fishing ground, Sylvester Manor has since 1652 been home to eleven generations of its original European settler family. It reflects a remarkably intact history of America's evolving tastes, economies and landscapes. Over time, the place has been transformed from a slaveholding provisioning plantation to an Enlightenment-era farm, then to a pioneering food industrialist's estate and today to an organic educational farm responsive to, and supported by, our neighbors and friends worldwide.Read more
Shelter Island Craft BreweryRead more
Shelter Island Tennis CourtShelter Island Tennis Club is a family-oriented tennis club on Shelter Island in the Hamptons, dedicated to teaching adults and children of all ages and abilities, the love and skills of tennis and fitness. We offer 10 And Under tennis to ages 4-6, a Junior Academy to kids ages 7-18, as well as clinics and lessons to adults. If you can't make it to the club our "Tennis to Go" option will send a pro to you so your home.Read more
Shelter Island Whale's Tale32 flavors of Hershey's premium ice cream, soft serve, yogurts, homemade cannoli, food, coffees, shakes & signature drinks! 18 hole nauticaly themed lighted mini-golf, private tennis court rentals, beautiful outdoor scenic patio, indoor AC seating, arcade room, kiddie rides, bath rooms & ATM. Hosting parties & events! Large parking lot. Open 7 days a week, seasonally May-October 631 749 1839Read more
Handwerklab Art GalleryCeramic fine art, modern jewelry, driftwood tables, bamboo lights. Objects, furnishings and fine art for the modern and traditional home. Locally sourced, hand-made objects ranging from fine silver jewelry to a comprehensive collection of indigenous artifacts. Nationally renown ceramic pinch potter John Pagliaro.Read more
Frequently Asked Questions about Shelter Island hotels
- Baron's Cove, Harborfront Inn at Greenport, and Hotel Moraine are some of the most popular hotels for travelers looking to stay near Mashomack Preserve. See the full list: Hotels near Mashomack Preserve.
- Popular hotels close to Sylvester Manor Educational Farm include Shelter Island House, Dering Harbor Inn, and The Pridwin Hotel and Cottages. See the full list: Hotels near Sylvester Manor Educational Farm.
- Popular luxury hotels in Shelter Island include Shelter Island House, The Pridwin Hotel and Cottages, and Sunset Beach. See the full list: Shelter Island Luxury Hotels.
- Popular hotels close to New Haven Airport include The Blake Hotel, The Study at Yale, and Graduate New Haven. See the full list: Hotels near New Haven Airport.
- A few of the most popular hotels near Shelter Island Historical Society are Shelter Island House, Dering Harbor Inn, and Sunset Beach. See the full list: Hotels near Shelter Island Historical Society.
- Some of the most popular pet-friendly hotels in Shelter Island are Shelter Island House, Ram's Head Inn, and Sunset Beach. See the full list: Pet Friendly Hotels in Shelter Island.
- Popular cheap hotels in Shelter Island include Shelter Island House, Dering Harbor Inn, and The Pridwin Hotel and Cottages. See the full list: Cheap Hotels in Shelter Island.
- Popular hotels by the beach in Shelter Island include The Pridwin Hotel and Cottages, Ram's Head Inn, and Sunset Beach. See the full list: Shelter Island Beach Hotels.
- Shelter Island House, Dering Harbor Inn, and The Pridwin Hotel and Cottages received great reviews from travelers looking for a romantic hotel in Shelter Island. See the full list: Romantic Hotels in Shelter Island.
- Some of the most popular hotels with a pool in Shelter Island include Shelter Island House, Dering Harbor Inn, and The Pridwin Hotel and Cottages. See the full list: Hotels with a Pool in Shelter Island.
The above hotel descriptions were created by AI, using information and phrases commonly found in reviews users submitted to Tripadvisor. Tripadvisor did not create and is not responsible for any of the above hotel descriptions. Please read full traveler reviews for more details and information. If you believe something in one of these AI-generated descriptions is inaccurate, please share your feedback.