Find hotels in Shelter Island, NY from 2.810.545 ₫

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Check prices for these dates

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Shelter Island hotels

Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (879)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Front of property – evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1272)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is 3.642.685 ₫
4.676.094 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
Indoor pool, outdoor pool
Hyatt Place Long Island East End

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 2.891.020 ₫
3.302.989 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Long Island East End
Property grounds
Pier Blue Inn Old Saybrook - Essex

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, (1001)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex
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
Old Saybrook
7.8 out of 10, Good, (1001)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is 2.658.424 ₫
3.057.188 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn Old Saybrook - Westbrook
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (711)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
Ocean View 2 Queens | Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (85)
"Hotel was beautiful !!"
United States
Erica
The price is 3.051.340 ₫
4.987.516 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Offshore Montauk
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.344.756 ₫
3.030.551 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hamlet Inn
Exterior
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
Old Saybrook
7.2 out of 10, Good, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is 1.761.682 ₫
2.025.934 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (405)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is 3.288.550 ₫
3.783.450 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (600)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 3.415.181 ₫
4.617.376 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sound View Greenport
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (549)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.552.012 ₫
4.772.780 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
The Harbor Front Inn
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is 2.736.745 ₫
3.127.033 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
House on Chase Creek
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is 2.049.996 ₫
2.357.495 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Clinton Motel
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (975)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Garden Suite King | Premium bedding, down duvets, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is 4.875.048 ₫
5.569.743 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Shoals Suites and Slips
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is 4.234.030 ₫
5.888.331 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
The Sagaponack
Outdoor pool, pool loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (290)
"Daunts is our home away from home when we visit Montauk. From the convenience to the superb hospitality and comfortable rooms. If you’re visiting MTK you have to stay at Daunts, and their pet friendly "
United States
Yohayna
Daunt's Albatross Motel
Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is 4.178.838 ₫
4.805.664 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Inn at Harbor Hill Marina
Front of property
The Preston House & Hotel

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (373)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is 4.137.050 ₫
4.726.580 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Preston House & Hotel
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, 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 Shelter Island Historical Society and Sunset 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.

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.

Stay near popular Shelter Island attractions

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.
See properties
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

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
"Hotel was beautiful !!"
Erica 1-night trip
Posted 3 days ago
Offshore Montauk

More cheap stays in Shelter Island

Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

30 Lake Avenue Riverhead NY
The price is 2.459.995 ₫ per night from 27 Dec to 28 Dec
2.459.995 ₫
2.810.545 ₫ total
27 Dec - 28 Dec
includes taxes & fees
6.6/10 (782 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.