Photo by Erisa Dilo

Hotels in Shelter Island Heights

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
May 16 - May 17
Tomorrow
May 17 - May 18
This weekend
May 16 - May 18
Next weekend
May 23 - May 25

Where to stay in Shelter Island Heights?

The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (29)
$431 nightly
The price is $493
May 17 - May 18
Total includes taxes and fees
The Chequit
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.
trending_down

Our prices for hotels in Shelter Island Heights are cheapest in March

See average prices and weather for all months

Price trends for hotels in Shelter Island Heights

Pricing is based on two traveler single night rates
May
$462
Average price during May is $462
Jun
$517
Average price during June is $517
Jul
$707
Average price during July is $707
Aug
$813
Average price during August is $813
Sep
$588
Average price during September is $588
Oct
$509
Average price during October is $509
Nov
$447
Average price during November is $447
Dec
$385
Average price during December is $385
Jan
$281
Average price during January is $281
Feb
$293
Average price during February is $293
Mar
$266
Average price during March is $266
Apr
$283
Average price during April is $283
Currently viewing crowd sizes and weather for May.

May

trending_flatModerate crowds
High 59°F / low 53°F. Sunny most days.
59°
weather_sun
May, Moderate crowds, average high temperature 59 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
68°
weather_sun
June, High crowds, average high temperature 68 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
62°
76°
weather_sun
July, High crowds, average high temperature 76 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
71°
76°
weather_sun
August, High crowds, average high temperature 76 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
71°
71°
weather_sun
September, High crowds, average high temperature 71 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
63°
weather_sun
October, Moderate crowds, average high temperature 63 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
54°
weather_sun
November, Moderate crowds, average high temperature 54 degrees Fahrenheit, average low temperature 46 degrees Fahrenheit. Sunny most days.
46°
46°
weather_cloudy
December, Low crowds, average high temperature 46 degrees Fahrenheit, average low temperature 38 degrees Fahrenheit. Cloudy most days.
38°
40°
weather_partly_sunny
January, Low crowds, average high temperature 40 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Partly sunny.
31°
40°
weather_cloudy
February, Low crowds, average high temperature 40 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Cloudy most days.
32°
43°
weather_partly_sunny
March, Low crowds, average high temperature 43 degrees Fahrenheit, average low temperature 36 degrees Fahrenheit. Partly sunny.
36°
50°
weather_sun
April, Moderate crowds, average high temperature 50 degrees Fahrenheit, average low temperature 44 degrees Fahrenheit. Sunny most days.
44°
Monthly weather averages (˚F)
View all properties

Top landmarks in Shelter Island Heights

Sunset Beach

Whether you want to hunt for sand dollars or smell the fresh air, Sunset Beach is a spot you might want to check out, located 0.9 mi (1.4 km) from central Shelter Island Heights. Catch the sunset by the shore at Crescent Beach, just a short walk away.

See properties in Sunset Beach
Sunset Beach

Learn more about Shelter Island Heights

Shelter Island Heights is well-known for its attractions such as Sunset Beach and Crescent Beach. This beachside city has something for everyone including sights like Shelter Island Country Club and Sylvester Manor.

See all hotels in Shelter Island Heights
View from the back patio of The Dory Restaurant on Shelter Island, NY #shelterisland #reflections #silence #nature
Photo by Erisa Dilo
Open Photo by Erisa Dilo
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
Sign in or join for free

Frequently asked questions

What accommodations do travelers recommend in Shelter Island Heights?
The Chequit is an accommodation that is popular with guests.
Where can I find free parking with my stay in Shelter Island Heights?
Park your car for free at West Neck Guesthouse.
Can I book a refundable hotel in Shelter Island Heights?
If you want the flexibility to change your travel plans to Shelter Island Heights, most accommodations offer refundable* rates you can book. You can find these accommodations by searching our site and using the “fully refundable” filter to narrow the results down.
Where can I stay with my pet in Shelter Island Heights?
Your animal companion is welcome at these pet-friendly hotels: The Rams Head Inn and The Chequit.
Which Shelter Island Heights hotels do our guests like for their central location?
Travelers like The Pridwin Hotel for its great location.
Where can I stay in Shelter Island Heights if I want a cheap accommodation?
An inexpensive option worth considering is Dering Harbor Inn.
Where can I stay in Shelter Island Heights if I want a vacation home instead of a traditional hotel?
If you want a good alternative to a hotel, review our selection of 48 vacation homes.
Where can I stay if I'm visiting Shelter Island Heights with my children?
Your kids are welcome at The Pridwin Hotel and Shelter Island House.
Where should I stay in Shelter Island Heights for a trip with my partner?
The Pridwin Hotel is a great option for a romantic getaway.
What will the weather in Shelter Island Heights be like during my visit?
The warmest months in Shelter Island Heights are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.
Why should I book my Shelter Island Heights hotel through Hotels.com?
There are plenty of reasons to book your Shelter Island Heights travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

https://www.hotels.com/lp/b/deals