Shelter Island hotels

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Booking Insights

Best Shelter Island hotels

These are the best prices for Jun 24 - 25.
Shelter Island House - Shelter Island - Bedroom
Parking
Free Wi-Fi
Pool
Pet friendly
Sunset Beach - Shelter Island - Bedroom
Sunset Beach
Shelter Island, NY
Free Wi-Fi
Pet friendly
Zey Hotel - Greenport
Parking
Free Wi-Fi
Pet friendly
The Menhaden - Greenport - Bedroom
Parking
Free Wi-Fi
Pet friendly
Faraway Sag Harbor - Sag Harbor - Building
Parking
Free Wi-Fi
Pool
Pet friendly
Hotel Moraine - Greenport - Building
Parking
Free Wi-Fi
Pool
Pet friendly

Popular filters in Shelter Island hotels

Hotels with parking
Shelter Island House, La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport and others
Hotels with free cancellation
Explore hotel deals with free cancellation in the area
Hotels with a pool
Shelter Island House, Sound View Greenport and 11 more
Booking Insights

KAYAK’s insights for hotels in Shelter Island

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Shelter Island with confidence.

What is the cheapest day of the week to book a hotel in Shelter Island?

Thursday offers the lowest rates in Shelter Island, with an average nightly price of $456/night. The highest prices are found on Tuesday, with average rates at $1,383/night.

How much is a hotel in Shelter Island for tonight?

The best deal for a 3-star hotel room in Shelter Island found by KAYAK users in the last 3 days was $574, while a 4-star hotel the lowest price was $214. The cheapest room found overall was for $214.

How much is a hotel in Shelter Island for this weekend?

The cheapest hotel room in Shelter Island for the upcoming weekend found on KAYAK in the last 3 days was for $782 per night. For the same dates, 3-star hotel rooms have been found for as low as $1,403 per night and 4-star hotel rooms from $782 per night.

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
July
$816
$1,008
Cheapest month to stay with an average 71% drop in price.
Most expensive month to stay with an average 56% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Shelter Island hotel deals

  • If you’re looking for a cheap hotel in Islip, you should consider visiting during the low season. You'll find cheaper accommodations in Islip in November and April.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Islip if you stay on a Tuesday. The opposite is true for, Wednesday, which is usually the most expensive day.
  • How long should you stay? KAYAK users usually book their accommodation in Islip for 2 days.
  • Hotels in Shelter Island provide convenient access to the region’s iconic landmarks, placing it among the most preferred holiday destinations. If you’re planning to visit the area soon, you won’t have a shortage of accommodation options. Reserve a room at the House on Chase Creek to experience the nightlife, arts, and trails.
  • For the two in love looking for that perfect hideout to formalize their marriage or on a romantic getaway, you won’t go wrong with Shelter Island. The city features many spots where you can hold an anniversary celebration or commemorate your honeymoon. Reserve a room at Shelter Island House near the island’s beautiful and secluded beaches.
  • Wade Beach should be your next stop if you’re with your family. From the fabulous views to the wide range of activities such as beachcombing, sunbathing, and fishing, the little ones will undoubtedly cherish every moment here. Sunset Beach and Dering Harbor Inn are recommended establishments to sleep in when touring Shelter Island.
  • To exploit Shelter Island’s splendor, plan and visit in the summer when the weather is pleasant, making it easy to see a wide range of outdoors. Head to the Mashomack Nature Preserve and explore the coastline and acres of fields, woodlands, and creeks. Spend a night at the Jake's 58 Hotel & Casino to be close to this mix of natural and human history.
  • Shelter Island is known for its business-oriented hotels, which are within a short range of the business district and corporate offices. Suppose you’re here to meet your new business associates or scout for a unique premise to set up your store. In that case, plan and sleep at Hilton Garden Inn Islip/MacArthur Airport.

FAQs when booking a hotel in Shelter Island

  • Where is the best place to stay on Shelter Island, close to dining options?

    Hotels in Shelter Island sit close to the area’s famous eateries such as The Islander, SALT Waterfront Bar & Grill, and Shelter Island Slice. Clarion Hotel & Conference Center is a great accommodation facility if you visit Shelter Island to sample local and upscale dishes.

  • What are the best hotels on Shelter Island for hiking and cycling?

    La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport lies within easy reach of The Mountaineer, Keene Valley, NY. This spot is ideal for through the woods. Therefore, clutch your rucksack on your shoulders and step out to trek along these beaten paths.

  • Which neighborhood in Shelter Island is best for enjoying the city’s art scene?

    Shelter Island is a region with a profound cultural heritage and rich traditional background. Don’t leave without exploring Shelter Island Historical Society. Step in and browse the rotating exhibits, including letters, diaries, deeds, and maps. A night at Hampton Inn Long Island-Brookhaven is a sure way of exploring this historic structure.

  • Which neighborhood in Shelter Island has the best nightlife?

    Shelter Island’s vibrant and relaxing nightlife provides a unique vibe that keeps visitors returning. Hampton Inn Long Island-Islandia is where you should sleep to experience the region’s nightly escapades. Bars, lounges, taverns, and clubs await. Whatever interests you.

  • How do I find a hotel in central Shelter Island?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Shelter Island districts. You can also do a search using the city map to choose a specific location, like Shelter Island city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Shelter Island hotels with free parking?

    There are many hotels in Shelter Island that offer both parking and free parking. Popular choices among KAYAK users include Shelter Island House, La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport and Zey Hotel.

Where to stay in Shelter Island?

Our map will help you find the perfect place to stay in Shelter Island by showing you the exact location of each hotel.