Search Motels in Shelter Island

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

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Shelter Island motels

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, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is AED 327
AED 423 total
includes taxes & fees
11 Dec - 12 Dec
Hamlet Inn
Exterior
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 AED 246
AED 283 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Property grounds
Clinton Motel

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is AED 286
AED 329 total
includes taxes & fees
7 Jan - 8 January 2026
Clinton Motel
Seasonal outdoor pool, pool umbrellas, sun loungers
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
Terrace/patio
Shorewood Inn

Shorewood Inn

2.5 star property
Riverhead
8.4 out of 10, Very Good, (708)
"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
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 AED 1,041
AED 1,190 total
includes taxes & fees
12 Dec - 13 Dec
The Hampton Maid
Outdoor pool, sun loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (287)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
Daunt's Albatross Motel
Exterior
Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut

2.5 star property
Clinton
6.4 out of 10, (228)
"Would stay again. "
United States
pamela
The price is AED 239
AED 275 total
includes taxes & fees
2 Jan - 3 January 2026
Lamplighter Motel - Clinton, Connecticut
Exterior
Sea Haven Resort Motel

Sea Haven Resort Motel

2.0 star property
Southampton
7.8 out of 10, Good, (31)
"Great staff"
United States
Douglas
The price is AED 443
AED 567 total
includes taxes & fees
13 Dec - 14 Dec
Sea Haven Resort Motel
View from room
Hero Beach Club

Hero Beach Club

4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is AED 526
AED 974 total
includes taxes & fees
18 Dec - 19 Dec
Hero Beach Club
Reception
Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

2.0 star property
Riverhead
6.6 out of 10, (779)
"Everything was good "
United States
Monica
The price is AED 382
AED 436 total
includes taxes & fees
14 Dec - 15 Dec
Budget Host East End Hotel in Riverhead
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

Top Shelter Island Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Yes"
Ray 1-night trip
Posted 1 day ago
The Harbor Front Inn

Frequently asked questions

What can I expect from a motel trip to Shelter Island?
If you're having trouble locating a motel in Shelter Island, consider some of the motels we suggest around the area or let us help you find a similar property from over 96 hotels and other accommodations. Simply filter using our search tools by price per night or cost-effective amenities such as free parking and free airport transportation.
What is a motel?
Motels often include free parking, and many have outdoor pools. Often one or two stories tall, motel properties usually have outdoor access to guestrooms from the parking lot. The term "motel" was conceived in 1925 in San Luis Obispo, California by the owner of the Milestone Mo-Tel.
What are the best motels in Shelter Island?
These are some of our customers' top motels to choose from in the larger area. Budget Host East End Hotel in Riverhead is located 20 mi (32.2 km) from the heart of Shelter Island. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking. Hamlet Inn: A seasonal outdoor pool, free WiFi, and free parking are available during your stay. Central Shelter Island is 13.9 mi (22.4 km) away. Bayview Resort: Enjoy access to the marina, and freebies including WiFi and parking. Located 17.6 mi (28.4 km) from the heart of Shelter Island. Econo Lodge Inn & Suites Old Saybrook Westbrook: Central Shelter Island is 15.5 mi (25 km) away. Free WiFi, free parking, and a terrace are available during your stay. Kenny's Tipperary Inn: 20.7 mi (33.3 km) from the heart of Shelter Island. Enjoy access to the seasonal outdoor pool, and freebies including WiFi and parking.
What things can I to do in Shelter Island?
These are some of the parks and outdoorsy places: Sunset Beach, Mashomack Preserve, and Crescent Beach. You'll find these family-friendly sights in the area: Shelter Island Whale's Tail, Railroad Museum of Long Island, and East End Seaport Maritime Museum. During your trip, here are some other places to visit: Shelter Island Historical Society, Gardiner's Bay Country Club, and Havens House.
What's the seasonal weather like in Shelter Island?
Weather can make or break a roadtrip, so we've gathered some data about year-round temperatures in Shelter Island to help you plan yours. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.
What are my options for getting around Shelter Island when staying in a motel?
We've gathered some information about local transportation options in Shelter Island to help you navigate your stay: Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. Otherwise, look for flights into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.