---
title: "Shelter Island Vacation Packages 2026 from $330 | Expedia"
description: "Bundle Shelter Island flight + hotel & save up to 100% off your flight with Expedia. Filter packages by price, amenities & location. FREE cancellation on select hotels."
canonical: "https://www.expedia.com/Shelter-Island.d157359.Destination-Travel-Guides"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-13T12:34:43Z
---

# Shelter Island Vacations from $330
![A wooden gazebo by a pond with a large tree trunk nearby.](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

## Book a Hotel + Flight or Car together to unlock savings

- ## Plan, book, travel with confidence
- ### Better together
Save up to $2,000 when you book a flight and hotel together\*
- ### Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ### Rest easy
Plan, book, and manage your trip all in one place

## Your Shelter Island Vacation

Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like [67 Steps Beach](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction), [Railroad Museum of Long Island](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction) and [Kontokosta Winery](https://www.expedia.com/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction). Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.

## The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Trip length

3 nights4 nights5 nights6-7 nights

Stars

5 star4 star & up3 star & up2 star & up

Flight class

EconomyPremium economyBusinessFirst class

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- ![The exterior of Hotel St. James with a prominent entrance, a sign for Connelly's Pub, and a view of the street.](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A room with a large window, a sofa, two armchairs, a vase with flowers, and a lamp.](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/3fbe1400.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 14 - Jan 17**

### [Hotel St. James + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-14/2027-01-17/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1144474&dealMarker=&paandie=true&cabinClass=e)
Manhattan
3 nights

**8.8/10** \- Excellent (8,205 reviews)
"Location location location! No-frills hotel right off of Times Square with large rooms (for Manhattan). Building is showing its age but doesn't feel dirty or run down. I'd call it "charming". Heating/AC unit is very noisy. Elevators can get crowded at checkout time."
Reviewed November 12, 2026
Roundtrip • Atlanta (ATL) - New York (JFK)
ATL - LGA • Nonstop LGA - ATL • Nonstop
[~~$519~~](https://www.expedia.com/)

**$330**
per traveler
found 1 day ago
- ![A rooftop terrace with outdoor seating, a city view, and a brick building.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/9118c9d6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A breakfast table with various dishes, a bottle of champagne, and a city view.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/fc228e9d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 1 - Jan 5**

### [JW Marriott Essex House New York + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-01/2027-01-05/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534143&dealMarker=&paandie=true&cabinClass=e)
Manhattan
4 nights

**8.8/10** \- Excellent (1,000 reviews)
Roundtrip • Atlanta (ATL) - New York (JFK)
ATL - LGA • Nonstop LGA - ATL • 1 stop
Save 100% on your flight
[~~$1,685~~](https://www.expedia.com/)

**$986**
per traveler
found 2 days ago
- ![A modern indoor seating area with wicker furniture, a large sofa, and a coffee table.](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/3215939b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A spacious indoor area with multiple seating arrangements, including tables and benches, and a central column with hanging lights.](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 16 - Jan 19**

### [INNSiDE by Meliá New York Nomad + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-19/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12627948&dealMarker=&paandie=true&cabinClass=e)
Manhattan
3 nights

**9.2/10** \- Wonderful (2,371 reviews)
"Fantastic place to stay! Room was very comfortable and a normal, large size. The complimentary espresso machine, water and mini bar items made the stay extremely welcoming! I will definitely be staying there again. Highly recommended."
Reviewed November 12, 2026
Roundtrip • Atlanta (ATL) - New York (JFK)
ATL - JFK • Nonstop JFK - ATL • Nonstop
[~~$711~~](https://www.expedia.com/)

**$452**
per traveler
found 1 day ago
- ![A grand staircase with ornate railings and patterned carpet, leading to a large arched window with a view of buildings.](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/w1500h982x0y0-71ef47cf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A high-rise interior with a modern living area featuring a sofa, chairs, and a coffee table, with a cityscape view through large windows.](https://images.trvl-media.com/lodging/1000000/10000/4900/4818/3a840840.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 16 - Jan 19**

### [Lotte New York Palace + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-19/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4818&dealMarker=&paandie=true&cabinClass=e)
Manhattan
3 nights

**9.0/10** \- Wonderful (2,370 reviews)
"Perfect location."
Reviewed November 12, 2026
Roundtrip • Atlanta (ATL) - New York (JFK)
ATL - JFK • Nonstop JFK - ATL • Nonstop
Save 100% on your flight
[~~$956~~](https://www.expedia.com/)

**$619**
per traveler
found 1 day ago
- ![A rooftop lounge with a striped ceiling, large windows, and a city view.](https://images.trvl-media.com/lodging/1000000/10000/2800/2714/c10117f0.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)
![A sunlit room with a large window, a sofa, chairs, a coffee table, and various potted plants.](https://images.trvl-media.com/lodging/1000000/10000/2800/2714/62bc89ae.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium)

**Jan 16 - Jan 19**

### [Park Lane New York + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-16/2027-01-19/?FromAirport=ATL&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2714&dealMarker=&paandie=true&cabinClass=e)
Manhattan
3 nights

**8.4/10** \- Very good (1,852 reviews)
Roundtrip • Atlanta (ATL) - New York (JFK)
ATL - JFK • Nonstop JFK - ATL • Nonstop
Save 100% on your flight
[~~$956~~](https://www.expedia.com/)

**$620**
per traveler
found 1 day ago

## Where to stay in and around Shelter Island

Shelter Island offers a tranquil escape with its charming waterfront and serene atmosphere. Ideal for outdoor adventures and romantic getaways, this small island invites travelers to explore its picturesque scenery. Discover the unique charm of this Rhode Island gem and enjoy unforgettable family-friendly excursions.

- [Greenport](#)
- [Noyack](#)
- [Sag Harbor](#)
- [Shelter Island Heights](#)
- [Southold](#)

![A pebbled beach at sunset with the sun setting over the horizon.](https://images.trvl-media.com/place/110728/52d32607-4fbb-4409-ba38-04d4ab724050.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Greenport](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=110728)

### Greenport

Greenport is the ultimate neighborhood for adventurous travelers seeking a blend of outdoor fun and romantic beach experiences. This charming city offers easy access to attractions like the scenic 67 Steps Beach, the intriguing Railroad Museum of Long Island, and the impressive Gardiner's Bay Country Club, ensuring memorable outings for couples and families alike. Located about 3 miles by car from Shelter Island, Greenport presents a smart choice for your stay, combining relaxation with a wealth of activities.

[See properties](https://www.expedia.com/Hotel-Search?regionId=110728)

![A lake surrounded by residential areas and a cloudy sky.](https://images.trvl-media.com/place/6217344/afbb79eb-e4b4-4bab-bfba-9659e0666fe3.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

Photo by Taozi

[View properties in map for Noyack](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=6217344)

### Noyack

Experience the charm of Noyack, an excellent hub for families and couples who want to enjoy a blend of outdoor and beach experiences. This quaint village is perfect for exploring local attractions like Sag Harbor Marine Park, the Sag Harbor Whaling and Historical Museum, and Foster Memorial Town Beach, offering something for everyone. Located about 6 miles by car from Shelter Island, Noyack is a smart choice for those seeking a relaxing getaway.

[See properties](https://www.expedia.com/Hotel-Search?regionId=6217344)

![A marina with several boats docked, a community bandstand, and a restaurant named American Legion.](https://images.trvl-media.com/place/154327/43eaeab6-df84-4715-8473-09dcfbf9fc6c.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Sag Harbor](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=154327)

### Sag Harbor

Make your vacation planning effortless by staying in Sag Harbor, a haven for families and couples thanks to its charming beaches and rich history. Visitors can enjoy the scenic East Hampton Main Beach, explore the fascinating Sag Harbor Whaling and Historical Museum, or unwind at the Sag Harbor Marine Park. Located about 5 miles by car from Shelter Island, Sag Harbor offers a perfect blend of relaxation and adventure, making it an excellent choice for your getaway.

[See properties](https://www.expedia.com/Hotel-Search?regionId=154327)

![A pebbled beach with a sunset and a distant bridge.](https://images.trvl-media.com/place/183716/f3da51ab-d07a-4450-8713-bade86cd14f7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Shelter Island Heights](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=183716)

### Shelter Island Heights

Shelter Island Heights stands out as a prime spot for travelers seeking a romantic getaway, family adventures, or a connection with nature. This charming destination offers easy access to beautiful beaches like the renowned 67 Steps Beach, the intriguing Railroad Museum of Long Island, and the scenic Gardiner's Bay Country Club for golf enthusiasts. Located about 1 mile by car from Shelter Island, it provides a convenient base to explore the area’s outdoor activities. Choosing Shelter Island Heights for your stay ensures a memorable vacation experience.

[See properties](https://www.expedia.com/Hotel-Search?regionId=183716)

![A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.](https://images.trvl-media.com/place/183719/b634a311-72c8-4775-8993-a7fef52c97ee.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[View properties in map for Southold](https://www.expedia.com/Hotel-Search?pwaOverlay=map&regionId=183719)

### Southold

Travelers visiting the area often choose Southold, especially families and couples seeking close proximity to natural beauty and recreational activities. This charming city offers a delightful mix of outdoor adventures, from the stunning Hamptons Beaches to the engaging Railroad Museum of Long Island. With a variety of attractions like 8 Hands Farm for art enthusiasts, Southold is a great base for a memorable vacation. Located about 5 miles by car from Shelter Island, Southold makes for a smart choice for your stay.

[See properties](https://www.expedia.com/Hotel-Search?regionId=183719)

## Discover the most popular places to visit in Shelter Island

### Shell Beach
![A close-up of a beach with various shells and pebbles.](https://images.trvl-media.com/place/553248621554204761/5a57054c-a374-4fe2-8982-2385bf184bb1.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 10.0/10 (1 review)

This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbor waters and more dynamic waves, perfect for beachcombing and wildlife spotting.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204761)

### Wades Beach
![A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.](https://images.trvl-media.com/place/553248621554204759/ee48f50e-5c27-4bcd-8a17-a99baf567092.jpg?impolicy=fcrop&w=960&h=640&p=1&q=medium)

Rating: 10.0/10 (1 review)

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](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204759)

### Shelter Island Historical Society

Rating: 8.0/10 (1 review)

This historic museum preserves Shelter Island's maritime heritage through artifacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248635961235094)

### Gardiner's Bay Country Club

This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbor. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6282173)

### Mashomack Preserve

Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6224462)

### Menhadden Lane Beach

Rating: 8.8/10 (3 reviews)

This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=553248621554204760)

### Havens House

Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.

[See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests&regionId=6232745)

## Shelter Island Hotel Deals

### [The Chequit](https://www.expedia.com/Shelter-Island-Heights-Hotels-The-Chequit.h67569836.Hotel-Information)

![An outdoor patio area with string lights, tables, chairs, and a fire pit.](https://images.trvl-media.com/lodging/68000000/67570000/67569900/67569836/e8baba10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 23 Grand Ave, Shelter Island Heights, NY, 11965, US
- Location: 1.4 mi from Shelter Island
- Star rating: 3/5
- Guest rating: 9/10 (Wonderful, 78 reviews)
- Price: $167 nightly, $191 total, Dec 13 - Dec 14, Total with taxes and fees
- Review: We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got.

### [Silver Sands Motel & Beach Bungalows](https://www.expedia.com/Greenport-Hotels-Silver-Sands.h91068954.Hotel-Information)

![A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.](https://images.trvl-media.com/lodging/92000000/91070000/91069000/91068954/ff9196d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 1400 Silvermere Rd, Greenport, NY, 11944, US
- Location: 2.7 mi from Shelter Island
- Star rating: 4/5
- Guest rating: 10/10 (Exceptional, 192 reviews)
- Price: $185 nightly, $211 total, Dec 13 - Dec 14, Total with taxes and fees
- Review: Amazing place to stay with a great location. We will definitely be back!

### [House on Chase Creek](https://www.expedia.com/Shelter-Island-Heights-Hotels-House-On-Chase-Creek.h12610909.Hotel-Information)

![A conservatory with a dining table set for four, surrounded by wooden chairs, with a view of trees and a lawn.](https://images.trvl-media.com/lodging/13000000/12620000/12611000/12610909/ae8f0ca6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 3 Locust Avenue, Shelter Island Heights, NY, 11965, US
- Location: 1.2 mi from Shelter Island
- Star rating: 2.5/5
- Guest rating: 9.4/10 (Exceptional, 87 reviews)
- Price: $185 nightly, $211 total, Nov 16 - Nov 17, Total with taxes and fees
- Review: Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!

### [The Harbor Front Inn](https://www.expedia.com/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![The entrance to The Harbor Front Inn with a double door and the address number 209.](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/0715a258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 209 Front St, Greenport, NY, 11944, US
- Location: 2.6 mi from Shelter Island
- Star rating: 3.5/5
- Guest rating: 9/10 (Wonderful, 676 reviews)
- Price: $148 nightly, $169 total, Dec 13 - Dec 14, Total with taxes and fees
- Review: Clean and comfortable room. Great location to walk around town. Nice continental breakfast.

### [Zey Hotel](https://www.expedia.com/Greenport-Hotels-The-Gallery-Hotel.h15622089.Hotel-Information)

![A two-story house with a balcony, outdoor seating area, and a variety of plants.](https://images.trvl-media.com/lodging/16000000/15630000/15622100/15622089/f2951978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 439 Main Street, Greenport, NY, 11944, US
- Location: 2.7 mi from Shelter Island
- Star rating: 3.5/5
- Guest rating: 9.2/10 (Wonderful, 449 reviews)
- Price: $143 nightly, $163 total, Dec 14 - Dec 15, Total with taxes and fees
- Review: Great place to stay for a walkable visit to Greenport NY. Comfy bed, great rooms for hanging out, close to everything.

### [The Shoals Suites and Slips](https://www.expedia.com/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 61600 Main Rd, Southold, NY, 11971, US
- Location: 3.4 mi from Shelter Island
- Star rating: 3.5/5
- Guest rating: 9.4/10 (Exceptional, 351 reviews)
- Price: $210 nightly, $237 total, Nov 29 - Nov 30, Total with taxes and fees
- Review: The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing.

### [Oyster Estate](https://www.expedia.com/Greenport-Hotels-Oyster-Estate.h90308554.Hotel-Information)

![A cozy interior with a bar area, seating, and a fireplace.](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/354e2975.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 326 Front St, Greenport, NY, 11944, US
- Location: 2.7 mi from Shelter Island
- Star rating: 4/5
- Guest rating: 9.2/10 (Wonderful, 302 reviews)
- Price: $183 nightly, $210 total, Dec 13 - Dec 14, Total with taxes and fees

### [Sound View Greenport](https://www.expedia.com/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![A spacious room with wicker furniture, large windows, and a view of the sea.](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Address: 58775 County Rd 48, Greenport, NY, 11944, US
- Location: 3.6 mi from Shelter Island
- Star rating: 4/5
- Guest rating: 8.4/10 (Very good, 768 reviews)
- Price: $174 nightly, $199 total, Dec 14 - Dec 15, Total with taxes and fees
- Review: "Location is nice. But many times booked for weddings so you won’t be able to go to the bar etc. The rooms are clean and fine but for the pricing I expected nicer. Feels more like a cabin. They also have fees that are not represented on an app like Expedia if you book through them. An additional 30 for overnight parking when you are paying 600 a night for a mediocre room on Long Island in November you would expect that to be included. Overall would not stay again there are much better options....

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.

[See all properties in Shelter Island](https://www.expedia.com/Hotel-Search?startDate=2026-11-27&endDate=2026-11-28&regionId=157359&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Find out more about Shelter Island

### Things to do near Shelter Island

Shelter Island offers a perfect getaway for outdoor enthusiasts and couples alike, featuring activities like golfing, skiing, and music concerts. Enjoy a relaxing beach experience with beach chairs for your comfort. Whether you're planning a day trip or a longer vacation, Shelter Island provides a charming atmosphere for those seeking a romantic beach retreat.

**Shopping**

If you're up for a drive, you can find great shopping options at the [Greenport Farmers' Market](https://www.expedia.com/Greenport-Farmers-Market-Greenport.d553248621532665744.Vacation-Attraction), located 3 miles away, for fresh local produce and unique gifts. [The Style Bar](https://www.expedia.com/The-Style-Bar-Sag-Harbor.d553248621532665737.Vacation-Attraction) and [BookHampton](https://www.expedia.com/BookHampton-Sag-Harbor.d553248621532665731.Vacation-Attraction), both 5 miles away, offer stylish apparel and a cozy selection of books, respectively.

**Recreation**

At [Bay Street Theatre](https://www.expedia.com/Bay-Street-Theatre-Sag-Harbor.d6326787.Vacation-Attraction), enjoy a captivating performance that blends culture and entertainment, creating a romantic atmosphere for couples or families. [Noyac Golf Club](https://www.expedia.com/Noyac-Golf-Club-Sag-Harbor.d6064499.Vacation-Attraction) offers a refreshing outdoor experience with its scenic golf course, while [Cedar Point County Park](https://www.expedia.com/Cedar-Point-County-Park-East-Hampton.d6326834.Vacation-Attraction) provides serene trails perfect for wellness and relaxation in nature.

**Adventure**

At [Splish Splash Water Park](https://www.expedia.com/Splish-Splash-Water-Park-Calverton.d6173416.Vacation-Attraction), located 23 miles from Shelter Island, enjoy thrilling water slides and family-friendly attractions for an exciting day out. For arcade fun, [Stay and Play LLC](https://www.expedia.com/Stay-And-Play-LLC-Old-Saybrook.d553248621532665775.Vacation-Attraction), 16 miles away, offers games and activities perfect for adventurous families. Explore the scenic [Walking Dunes Trailhead](https://www.expedia.com/Walking-Dunes-Trailhead-Montauk.d553248633992587102.Vacation-Attraction), also 16 miles away, for a refreshing hike.

**Nightlife**

Shelter Island offers a laid-back nightlife with cozy bars and intimate lounges. Enjoy live music at local venues, sip craft cocktails at waterfront spots, or unwind at a beach bonfire. The atmosphere is relaxed, perfect for mingling with locals and fellow travelers under the stars.

### Find the best attractions in and around Shelter Island

Located in New York, Shelter Island is a charming destination perfect for outdoor and romantic beach vacations. Visitors can explore beautiful spots like Crescent Beach and Hay Beach, alongside historic buildings and urban parks. The area offers a rich blend of culture and outdoor experiences, making it ideal for travelers seeking relaxation and adventure in a picturesque setting.

- **[67 Steps Beach: ](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction)** Experience the serene beauty of 67 Steps Beach, just 4 miles from Shelter Island. With its inviting beach vibes, it's a perfect spot for sunbathing, swimming, or a peaceful stroll along the shore, offering a relaxing escape into nature.
- **[Gardiner's Bay Country Club: ](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction)** Nestled within Shelter Island, Gardiner's Bay Country Club is a golfer's paradise. Enjoy a round of golf on its stunning course, surrounded by picturesque views and lush landscapes, making it an ideal spot for both seasoned players and beginners alike.
- **[Orient Point County Park: ](https://www.expedia.com/Orient-Point-County-Park-Orient.d553248621532665781.Vacation-Attraction)** Located 8 miles from Shelter Island, Orient Point County Park is a family-friendly urban park. With ample outdoor activities, picnic areas, and scenic views, it’s a great destination for families looking to enjoy nature and city vibes simultaneously.

### Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

### Tips to save on your trip to Shelter Island

- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Shelter Island.
- Consider traveling to Shelter Island during the low season (January to March) for more affordable options.
- Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget.
- Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties.

## Frequently Asked Questions

### Is Shelter Island better suited for a beach vacation or a cultural trip?

Shelter Island is primarily an outdoor and nature destination, making it well-suited for a beach vacation. The island is known for its scenic views and offers numerous beaches, such as [Sunset Beach](https://www.expedia.com/Sunset-Beach.d553248626388141313.Vacation-Attraction), located about 3 miles from the center, and [Wades Beach](https://www.expedia.com/Wades-Beach.d553248621554204759.Vacation-Attraction), about 1 mile away, providing ample opportunities for enjoying the water and coastal scenery.

While beaches are a highlight, a Shelter Island vacation can also include recreational and natural attractions. You can visit [Gardiner's Bay Country Club](https://www.expedia.com/Gardiners-Bay-Country-Club.d6282173.Vacation-Attraction) for golf, about 1 mile from the center, or explore the [Mashomack Preserve](https://www.expedia.com/Mashomack-Preserve.d6224462.Vacation-Attraction), a significant nature area about 3 miles away. For a taste of local flavor, [Peconic Bay Winery](https://www.expedia.com/Peconic-Bay-Winery.d553248621532665640.Vacation-Attraction) is about 16 miles from central Shelter Island.

### How can I save money on a Shelter Island vacation package?

When you bundle, you can save up to 30%\*. To save money on a Shelter Island package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. \*Members only. Savings vary.

### What are the top things to do in Shelter Island?

A Shelter Island vacation offers a blend of natural beauty and outdoor activities:

Browse and book [things to do in Shelter Island](https://www.expedia.com/Things-To-Do-In-Shelter%20Island.d157359.Travel-Guide-Activities) on Expedia.

### Do you need to rent a car in Shelter Island, or is public transport enough?

A rental car is highly recommended for a Shelter Island vacation package, as the island is primarily an outdoor and nature destination with attractions spread out. While walking and riding a bike are options for shorter distances, a car provides the most flexibility to explore the island's various beaches and natural sights.

Having a car allows you to easily reach popular spots like [Sunset Beach](https://www.expedia.com/Sunset-Beach.d553248626388141313.Vacation-Attraction) or the expansive [Mashomack Preserve](https://www.expedia.com/Mashomack-Preserve.d6224462.Vacation-Attraction). For Shelter Island vacation packages with flights, a rental car allows you to fully experience all the island has to offer, from its scenic views to its many outdoor activities.

### Can I change or cancel my Shelter Island vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

### Do One Key members get extra savings when booking Shelter Island vacation packages?

Yes, members who join our free [One Key™](https://www.expedia.com/welcome-one-key) travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

### Does Expedia offer Book Now, Pay Later Shelter Island vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by [Affirm](https://www.expedia.com/ega/lodging/625310), you can spread the cost of your Shelter Island vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

### How do I find last-minute vacation packages to Shelter Island?

To find last-minute vacation packages to Shelter Island, explore the [last-minute deals](https://www.expedia.com/lp/b/vacations/last-minute-deals) section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

### How does free cancellation work on Shelter Island vacation packages?

Free cancellation on a Shelter Island vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia [help center](https://www.expedia.com/helpcenter) for further details.

### Is it cheaper to book a Shelter Island vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Shelter Island getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

### Why should I book my Shelter Island vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

## Explore a world of travel with Expedia

- [Lodging](?equalTargetTab=tab-0)
- [Flights](?equalTargetTab=tab-1)
- [Packages](?equalTargetTab=tab-2)
- [Cars](?equalTargetTab=tab-3)
- [Vacation Rentals](?equalTargetTab=tab-4)
- [Things to Do](?equalTargetTab=tab-5)
- [Resorts & Hotels with Spas in Greenport](https://www.expedia.com/Greenport-Hotels-Spa-Hotel.0-0-d110728-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Hot Tubs in Shelter Island](https://www.expedia.com/Shelter-Island-Hotels-Hotels-With-Hot-Tubs.0-0-d157359-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Shelter Island](https://www.expedia.com/Shelter-Island-Hotels-Golf-Hotel.0-0-d157359-tGolfHotel.Travel-Guide-Filter-Hotels)
- [3 Star Hotels in Shelter Island](https://www.expedia.com/3Star-Shelter-Island-Hotels.s30-0-d157359.Travel-Guide-Filter-Hotels)
- [Sag Harbor Hotels](https://www.expedia.com/Sag-Harbor-Hotels.d154327.Travel-Guide-Hotels)
- [Southold Hotels](https://www.expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)
- [Hampton Bays Hotels](https://www.expedia.com/Hampton-Bays-Hotels.d183681.Travel-Guide-Hotels)
- [Riverhead Hotels](https://www.expedia.com/Riverhead-Hotels.d5993.Travel-Guide-Hotels)
- [Beach Hotels in Greenport](https://www.expedia.com/Greenport-Hotels-Beach-Hotel.0-0-d110728-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Resorts in Shelter Island](https://www.expedia.com/Shelter-Island-Resorts.d157359-aaResorts.Travel-Guide-Accommodation)
- [Orient Hotels](https://www.expedia.com/Orient-Hotels.d6326191.Travel-Guide-Hotels)
- [B&B in Hamptons](https://www.expedia.com/Hamptons-Bed-And-Breakfast.d6056452-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Shelter Island](https://www.expedia.com/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)
- [East Hampton Hotels](https://www.expedia.com/East-Hampton-Hotels.d1524.Travel-Guide-Hotels)
- [Montauk Hotels](https://www.expedia.com/Montauk-Hotels.d10637.Travel-Guide-Hotels)
- [Aparthotels in Shelter Island](https://www.expedia.com/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation)
- [Beach Hotels in Hamptons](https://www.expedia.com/Hamptons-Hotels-Beach-Hotel.0-0-d6056452-tBeachHotel.Travel-Guide-Filter-Hotels)
- [Bridgehampton Hotels](https://www.expedia.com/Bridgehampton-Hotels.d6130684.Travel-Guide-Hotels)
- [Houseboats in Shelter Island](https://www.expedia.com/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
- [Southampton Hotels](https://www.expedia.com/Southampton-Hotels.d6782.Travel-Guide-Hotels)
- [B&B in Shelter Island](https://www.expedia.com/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts & Hotels with Spas in Shelter Island](https://www.expedia.com/Shelter-Island-Hotels-Spa-Hotel.0-0-d157359-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Amagansett Hotels](https://www.expedia.com/Amagansett-Hotels.d73561.Travel-Guide-Hotels)
- [Cabin Rentals in Shelter Island](https://www.expedia.com/Shelter-Island-Cabins.d157359-aaCabins.Travel-Guide-Accommodation)
- [5 Star Hotels in Shelter Island](https://www.expedia.com/5Star-Shelter-Island-Hotels.s50-0-d157359.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Shelter Island](https://www.expedia.com/Shelter-Island-Hotels-Luxury-Hotel.0-0-d157359-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [B&B in Greenport](https://www.expedia.com/Greenport-Bed-And-Breakfast.d110728-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Vacation Homes in Shelter Island](https://www.expedia.com/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Greenport Hotels](https://www.expedia.com/Greenport-Hotels.d110728.Travel-Guide-Hotels)
- [Family Hotels in Shelter Island](https://www.expedia.com/Shelter-Island-Hotels-Family-Hotel.0-0-d157359-tFamilyHotel.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Shelter Island](https://www.expedia.com/4Star-Shelter-Island-Hotels.s40-0-d157359.Travel-Guide-Filter-Hotels)
- [Marriott Hotels & Resorts in Hamptons](https://www.expedia.com/Hamptons-Hotels-Marriott-Hotels-Resorts.0-0-d6056452--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels)
- [Hotels near Sunset Beach](https://www.expedia.com/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
- [Shelter Island Hotels](https://www.expedia.com/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)
- [Cottages in Shelter Island](https://www.expedia.com/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)
- [Flights from New York (NYC) to East Hampton (HTO)](https://www.expedia.com/lp/flights/nyc/hto/new-york-to-east-hampton)
- [Flights from New York (JFK) to East Hampton (HTO)](https://www.expedia.com/lp/flights/jfk/hto/new-york-to-east-hampton)
- [Flights from Boston (BOS) to East Hampton (HTO)](https://www.expedia.com/lp/flights/bos/hto/boston-to-east-hampton)
- [Flights to East Hampton](https://www.expedia.com/Cheap-Flights-To-East-Hampton.d1524.Travel-Guide-Flights)
- [Flights from MacArthur](https://www.expedia.com/lp/airports/isp/flights-from-macarthur-airport)
- [Flights to Shelter Island](https://www.expedia.com/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)
- [Flights to Hamptons](https://www.expedia.com/Cheap-Flights-To-Hamptons.d6056452.Travel-Guide-Flights)
- [Flights from East Hampton](https://www.expedia.com/lp/airports/hto/flights-from-east-hampton-airport)
- [Flights from Shelter Island](https://www.expedia.com/lp/flights/157359/flights-from-shelter-island)
- [Shinnecock Nation Cultural Center and Museum](https://www.expedia.com/Shinnecock-Nation-Cultural-Center-And-Museum-Southampton.d6327552.Vacation-Attraction)
- [Visit Montauk](https://www.expedia.com/Montauk.dx10637)
- [The Old Field Vineyards](https://www.expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction)
- [Visit Hampton Bays](https://www.expedia.com/Hampton-Bays.dx183681)
- [Gardiner's Bay Country Club](https://www.expedia.com/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction)
- [Havens House](https://www.expedia.com/Havens-House-Shelter-Island.d6232745.Vacation-Attraction)
- [Visit Southampton](https://www.expedia.com/Southampton.dx6782)
- [Longhouse Reserve](https://www.expedia.com/LongHouse-Reserve-East-Hampton.d6326942.Vacation-Attraction)
- [Havens Beach](https://www.expedia.com/Havens-Beach-Sag-Harbor.d6326903.Vacation-Attraction)
- [Elizabeth A. Morton National Wildlife Refuge](https://www.expedia.com/Elizabeth-A-Morton-National-Wildlife-Refuge-Sag-Harbor.d6326867.Vacation-Attraction)
- [Southold Vacations](https://www.expedia.com/Southold.d183719.Destination-Travel-Guides)
- [Visit Sag Harbor](https://www.expedia.com/Sag-Harbor.dx154327)
- [Bay Street Theatre](https://www.expedia.com/Bay-Street-Theatre-Sag-Harbor.d6326787.Vacation-Attraction)
- [Cooper's Beach](https://www.expedia.com/Coopers-Beach-Southampton.d6326842.Vacation-Attraction)
- [Truman's Beach](https://www.expedia.com/Trumans-Beach-New-York.d553248635941390090.Vacation-Attraction)
- [Visit Amagansett](https://www.expedia.com/Amagansett.dx73561)
- [Norman E. Klipp Marine Park](https://www.expedia.com/Norman-E-Klipp-Marine-Park-Greenport.d553248626388141305.Vacation-Attraction)
- [Sunset Beach](https://www.expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction)
- [Greenport Vacations](https://www.expedia.com/Greenport.d110728.Destination-Travel-Guides)
- [Camp Hero State Park](https://www.expedia.com/Camp-Hero-State-Park-Montauk.d6326821.Vacation-Attraction)
- [Foster Memorial Town Beach](https://www.expedia.com/Foster-Memorial-Town-Beach-New-York.d6326880.Vacation-Attraction)
- [Noyac Golf Club](https://www.expedia.com/Noyac-Golf-Club-Sag-Harbor.d6064499.Vacation-Attraction)
- [Sylvester Manor](https://www.expedia.com/Sylvester-Manor-Shelter-Island-Heights.d6282169.Vacation-Attraction)
- [Kontokosta Winery](https://www.expedia.com/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Oysterponds Historical Society](https://www.expedia.com/Oysterponds-Historical-Society-Orient.d6326266.Vacation-Attraction)
- [Camera Obscura](https://www.expedia.com/Camera-Obscura-Greenport.d6326819.Vacation-Attraction)
- [Sag Harbor Vacations](https://www.expedia.com/Sag-Harbor.d154327.Destination-Travel-Guides)
- [Orient Vacations](https://www.expedia.com/Orient.d6326191.Destination-Travel-Guides)
- [Railroad Museum of Long Island](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction)
- [Sag Harbor Marine Park](https://www.expedia.com/Sag-Harbor-Marine-Park-Sag-Harbor.d6327316.Vacation-Attraction)
- [67 Steps Beach](https://www.expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction)
- [Wolffer Estates Vineyard](https://www.expedia.com/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction)
- [East Hampton Main Beach](https://www.expedia.com/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction)
- [Visit Shelter Island](https://www.expedia.com/Shelter-Island.dx157359)
- [Mashomack Preserve](https://www.expedia.com/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction)
- [Visit Greenport](https://www.expedia.com/Greenport.dx110728)
- [Car rental Shelter Island](https://www.expedia.com/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)
- [Car rental East Hampton](https://www.expedia.com/Car-Rentals-In-East-Hampton.d1524.Car-Rental-Guide)
- [Enterprise Rental Cars in Shelter Island](https://www.expedia.com/Enterprise-Car-Rentals-In-Shelter-Island.d157359-c15.Car-Rental-Guide-Suppliers)
- [Car rental Southampton](https://www.expedia.com/Car-Rentals-In-Southampton.d6782.Car-Rental-Guide)
- [Car rental Greenport](https://www.expedia.com/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
- [Car rental Sag Harbor](https://www.expedia.com/Car-Rentals-In-Sag-Harbor.d154327.Car-Rental-Guide)
- [Luxury Car Rentals in Shelter Island](https://www.expedia.com/Luxury-Car-Rentals-In-Shelter-Island.d157359-tLuxury.Car-Rental-Guide-Class)
- [Hamptons Vacation Rentals](https://www.expedia.com/Hamptons-Vacation-Rentals.d6056452.Travel-Guide-VacationRentals)
- [Greenport Vacation Rentals](https://www.expedia.com/Greenport-Vacation-Rentals.d110728.Travel-Guide-VacationRentals)
- [Shelter Island Vacation Rentals](https://www.expedia.com/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)
- [Things to do in Greenport](https://www.expedia.com/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Shelter Island](https://www.expedia.com/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)
- [Things to do in East Hampton](https://www.expedia.com/Things-To-Do-In-East-Hampton.d1524.Travel-Guide-Activities)
- [Things to do in Sag Harbor](https://www.expedia.com/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities)
- [Things to do in Southampton](https://www.expedia.com/Things-To-Do-In-Southampton.d6782.Travel-Guide-Activities)
- [Things to do in Montauk](https://www.expedia.com/Things-To-Do-In-Montauk.d10637.Travel-Guide-Activities)
- [Things to do in Hamptons](https://www.expedia.com/Things-To-Do-In-Hamptons.d6056452.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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