Choose from 84 vacation rentals located in Shelter Island, New York. Top filters in Shelter Island include Air conditioner, Internet / Wifi, and Laundry. Prices range from $83 to $7,251 per night. Our most popular vacation rental types near Shelter Island are Condo and Hotel.

Top vacation rentals in Shelter Island

Property view
4.8
Outstanding(44 Reviews)
House
 in Shelter Island
Perfect Family Summer Vacation Home Close to beach 18x42 pool
6 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed

Experience the best of Shelter Island with this House available for $573. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Property view
4.5
Excellent(1 Review)
Inn
 in Shelter Island Heights
The Chequit
Garden · Pets allowed · Air conditioner

This Inn for $102 in Shelter Island, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
booking logo
View deal
Property view
House
 in Shelter Island
Ahoy There
8 guests · 4 bedrooms · 2 baths
Pool · Pets allowed · Family friendly

The best choice in Shelter Island for House, for $993 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
plumguide logo
View deal
Beachfront
Property view
4.3
Excellent(8 Reviews)
Hotel
 in Shelter Island
Rams Head Inn
Garden · Pets allowed · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Shelter Island, at $108 per night for your next great vacation.

$$$$
booking logo
View deal

Search by amenity

Explore vacation rentals with the most popular amenities in Shelter Island

Vacation rentals with air conditioning in Shelter Island

A heated pool
5.0
Outstanding(32 Reviews)
House
 in Shelter Island
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Indulge in a peaceful retreat at Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!, our elegant House in Shelter Island. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
city photo
Shelter Island

Shelter Island travel guide

Let us help you plan your perfect Shelter Island vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Shelter Island, and more.

Frequently asked questions

What do I need to know before visiting Shelter Island, NY?

Before visiting Shelter Island, NY, it is important to know about the local regulations and attractions. Here are some key points to remember:

  • Shelter Island has a strict noise ordinance from 10pm - 7am.
  • You must have a permit to drive on some of the beaches.
  • The town has a variety of restaurants, shops, and outdoor activities.

Overall, Shelter Island is a great place to visit for a relaxing getaway. Make sure to research the local regulations and attractions before your trip.

What are the must-visit tourist attractions in Shelter Island, NY?

Shelter Island, NY is a popular tourist destination with a variety of attractions to explore. Here are some of the must-visit attractions on the island:

  • Shelter Island Historical Society
  • Shelter Island Heights Park
  • Shelter Island Beach
  • Shelter Island Country Club
Visitors can also take a boat tour to explore the local waters, go fishing, or bird watching. There are also several parks, beaches, and nature trails to explore. Whether you're looking for a relaxing getaway or a fun outdoor adventure, Shelter Island has something for everyone.

How can I get around in Shelter Island, NY?

You can get around Shelter Island, NY in the following ways:

  • By car
  • By bike
  • By foot

You can also take a ferry from the North Fork of Long Island to get to Shelter Island.

Where can I find affordable accommodation in Shelter Island, NY?

Shelter Island, NY is a beautiful destination for a vacation, and luckily there are plenty of affordable accommodation options. Here are some great options for you to consider:

  • Ram's Head Inn: This charming inn is located in the heart of the island and offers comfortable rooms at reasonable prices.
  • Shelter Island House: This hotel is located on the waterfront and offers stunning views of the island.
  • Shelter Island Lodge: This lodge offers a variety of room options, from standard rooms to suites, all at affordable rates.
  • Shelter Island Inn: This inn offers cozy rooms and a great location close to the beach.

What is the culture like in Shelter Island, NY?

Shelter Island, New York is a small town located on the East End of Long Island. It is known for its beautiful beaches, quaint shops, and relaxed atmosphere. Here are five things that make the culture of Shelter Island unique:

  • The island is home to many artists and writers, who come to take advantage of the peaceful atmosphere.
  • The island has a rich history and is home to many historical sites, such as the Sylvester Manor and Gardiner’s Island.
  • The island has a strong sense of community, with many people coming together for events such as the Shelter Island 10K.
  • The island is known for its delicious seafood and local produce, which can be found at many of the island’s restaurants and farmers markets.
  • The island is also home to a variety of outdoor activities, such as kayaking, fishing, and hiking.

Is Shelter Island, NY safe to travel to?

Shelter Island, NY is generally safe to travel to. Here are some things to consider:

  • Research the local crime rate
  • Be aware of your surroundings
  • Take safety measures when traveling alone

What are the popular shopping destinations in Shelter Island, NY?

Popular shopping destinations in Shelter Island, NY include:

  • Shelter Island Pharmacy & Gift Shop
  • Shelter Island Hardware & Home Center
  • Shelter Island Grocery Store

What are the best neighborhoods to visit in Shelter Island, NY?

The best neighborhoods to visit in Shelter Island, NY are:

  • Dering Harbor
  • Shelter Island Heights
  • Ram Island

Each of these neighborhoods offer unique experiences, from beautiful waterfront views and luxury shopping in Dering Harbor to the relaxed atmosphere of Shelter Island Heights and the peaceful nature of Ram Island.

Where is Shelter Island, NY?

Shelter Island, NY is a small town located at the eastern end of Long Island in New York. It is nestled between the North and South Forks of Long Island, and is accessible by ferry from both Greenport and North Haven. Shelter Island is known for its beautiful beaches, lush forests, and quaint small-town charm.

What are the most popular vacation rental amenities in Shelter Island, NY?

The most popular vacation rental amenities in Shelter Island, NY include:

  • Outdoor recreation areas, such as pools, hot tubs, and patios
  • Modern kitchen appliances and amenities
  • Spacious living areas with comfortable furnishings
  • High-speed internet access
  • On-site laundry facilities

These amenities are designed to help visitors make the most of their stay in Shelter Island, NY, providing them with the comforts of home while they explore the area.

What are the top things to do in Shelter Island, NY?

Shelter Island, NY is the perfect destination for a summer getaway. Here are some of the top things to do while visiting:

  • Visit the Mashomack Preserve and explore the trails and wildlife
  • Take a boat tour of Coecles Harbor
  • Spend a day at Crescent Beach
  • Go kayaking or paddle boarding in the harbor
No matter what activity you choose, you're sure to have a great time in Shelter Island, NY.

What is the price range for rentals in Shelter Island?

Vacation rentals in Shelter Island have a price range between $83-$7,251. The average price for rentals in Shelter Island is $761 per night.

What are the most popular vacation rental amenities in Shelter Island?

  • Air conditioner
  • Internet / Wifi
  • Laundry

Explore near Shelter Island

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring