Find hotels in Shelter Island, NY from 2.820.062 ₫

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4 Dec - 5 Dec
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5 Dec - 6 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

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Top 10 Shelter Island hotels and places to stay

Front of property – evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is 3.655.298 ₫
4.692.284 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very good, (695)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
The price is 10.417.335 ₫
14.217.948 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Gurney's Montauk Resort & Seawater Spa
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1001)
"Excellent food, in addition to friendly and helpful staff."
United States
marybeth
The price is 8.148.639 ₫
10.030.210 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Saybrook Point Resort & Marina
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1009)
"We love the stay everything was perfect"
United States
angelica
The price is 4.227.592 ₫
5.316.665 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Water's Edge Resort & Spa
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

2.0 star property
Hampton Bays
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
Ocean View 2 Queens | Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
9.2 out of 10, Wonderful, (74)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is 3.061.905 ₫
5.004.783 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Offshore Montauk
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1000)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (540)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 2.935.315 ₫
4.644.293 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Harbor Front Inn
Exterior
Zey Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (290)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (973)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is 6.466.132 ₫
7.436.052 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Madison Beach Hotel
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is 2.667.427 ₫
3.067.541 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Quality Inn Old Saybrook - Westbrook
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (688)
"Great place to stay"
United States
Mitchell
The price is 7.476.745 ₫
8.542.181 ₫ total
includes taxes & fees
6 Dec - 7 Dec
The Hampton Maid
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (439)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.705.665 ₫
3.496.795 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Hamlet Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (390)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 2.911.358 ₫
3.352.599 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (596)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 5.133.504 ₫
7.155.724 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sound View Greenport
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (571)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is 5.102.788 ₫
5.829.935 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Sag Harbor Inn
View from room
Hero Beach Club

Hero Beach Club

4.0 star property
Montauk
9.0 out of 10, Wonderful, (201)
"Great weekend trip "
United States
Timothy
The price is 4.776.042 ₫
8.138.234 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Hero Beach Club
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1001)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is 3.061.673 ₫
3.497.961 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt Place Long Island East End
Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (211)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is 4.011.029 ₫
5.637.110 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Sagaponack
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 Shelter Island

Find the best Shelter Island areas for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island

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, Gardiner's Bay Country Club and Shelter Island Historical Society 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 Shelter Island Historical Society and Sunset Beach.

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Shelter Island Historical Society.

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.

Stay near popular Shelter Island attractions

Man watching sailboat on Long Island Sound

Wades Beach

Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
See properties
Colorful pebbles and shells on a beach

Shell Beach

This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
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Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Room was spotless. Bed was so comfortable! Robert, the he head of the house and front desk was a pleasure and made our stay so welcoming and enjoyable. "
Jennifer 1-night trip
Posted 11 days ago
Offshore Montauk

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Get rates
7.8/10 Good! (1,006 reviews)

Hotels in Shelter Island with star rating

Frequently asked questions

What's the seasonal weather in Shelter Island?
The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.

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