Photo by Brian V. Rowe

Find hotels in Shelter Island, NY from 2.813.219 ₫

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shelter Island hotels

Beach nearby
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (128)
"Easy parking. Walkable dining and to boardwalk. Quaint shopping."
United States
Kerry
The price is 2.320.718 ₫
2.668.826 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Niantic Inn
Golf
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (443)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.343.954 ₫
3.029.514 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hamlet Inn
Individually decorated, individually furnished, desk, laptop workspace
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, (460)
"🙂"
United States
Jared
The price is 1.763.693 ₫
2.028.247 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Ocean View 2 Queens | Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (81)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is 3.054.823 ₫
4.993.209 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Montauk
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, (878)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
The price is 2.051.946 ₫
2.359.738 ₫ total
includes taxes & fees
15 Jan - 16 Jan 2026
Clinton Motel
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, (1003)
"A welcoming place with some nice touches."
United States
Leslie
Pier Blue Inn Old Saybrook - Essex
Lobby
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1268)
"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 3.646.150 ₫
4.680.541 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Montauk Manor
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 2.739.869 ₫
3.130.602 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Exterior
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (710)
"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
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, (1004)
"The staff was friendly. The room was good. "
United States
Narida
The price is 2.660.953 ₫
3.060.096 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Old Saybrook - Westbrook
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

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
BBQ/picnic Area
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, (1002)
"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 2.946.944 ₫
3.366.885 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Hyatt Place Long Island East End
Lobby lounge
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.527.769 ₫
5.317.941 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Harbor Front Inn
Reception
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (397)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is 3.186.474 ₫
3.666.853 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 4.188.074 ₫
6.072.708 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Sound View Greenport
Property grounds
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is 2.107.191 ₫
2.423.269 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Liberty Inn
Terrace/patio
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
"The property was clean beautiful and pleasant. Loved the trendy decor."
United States
Jennifer
The price is 4.708.953 ₫
6.432.325 ₫ total
includes taxes & fees
22 Dec - 23 Dec
American Beech Hotel
Exterior
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, (228)
"Room was clean and comfortable. Easy check in and check out. Staff very accommodating. "
United States
James
The price is 4.879.686 ₫
5.575.043 ₫ total
includes taxes & fees
22 Dec - 23 Dec
The Shoals Suites and Slips
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, (1000)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is 4.182.813 ₫
4.810.235 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Inn at Harbor Hill Marina
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Crescent Beach and Sunset 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 Sunset Beach and Crescent 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 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.

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
"Excellent views. Quiet and calm "
Jonathan 1-night trip
Posted 6 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 2.462.335 ₫ per night from 21 Dec to 22 Dec
2.462.335 ₫
2.813.219 ₫ total
21 Dec - 22 Dec
includes taxes & fees
6.6/10 (780 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.

Explore a world of travel with Expedia