Title: Visit Shelter Island: Best of Shelter Island Tourism | Expedia Travel Guide - Expedia.ca

[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides)

# Shelter Island

## Travel Guide

![Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

[Photo by tom owens](https://mediaim.expedia.com/destination/2/57db4dbbb841fe5852df8ed4b2f64ec5.jpg)

![Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

[Photo by Rich Barton](https://mediaim.expedia.com/destination/2/1263ceec78a2ea3b58ee516bf8c95425.jpg)

## Visit Shelter Island

Where to stay

Things to do

### Where to stay in Shelter Island

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Silver Beach

 While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach. 

[](https://expedia.ca/Shelter-Island-Silver-Beach.dx553248635976481903)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Coecles Harbor

 When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area. 

[](https://expedia.ca/Shelter-Island-Coecles-Harbor.dx553248635976480820)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Menantic Creek

 If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach. 

[](https://expedia.ca/Shelter-Island-Menantic-Creek.dx553248635976481214)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Shorewood

 While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Sunset Beach. 

[](https://expedia.ca/Shelter-Island-Shorewood.dx553248635976481937)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Hay Beach

 Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out. 

[](https://expedia.ca/Shelter-Island-Hay-Beach.dx553248635976470037)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Montclair Colony

 While Montclair Colony isn't home to many top sights, Sunset Beach and Crescent Beach are some notable places to visit nearby. 

[](https://expedia.ca/Shelter-Island-Montclair-Colony.dx553248635976473165)

- Shelter Island Hotel Deals
- Vacation Rentals in Shelter Island

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $501

CA $684 total

Jan 6 - Jan 7, 2026

includes taxes & fees

Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...

8.2/10 Very Good! (697 reviews)

EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay.

Reviewed on Dec 8, 2025

[](https://expedia.ca/Hotel-Search?startDate=06%2F01%2F2026&endDate=07%2F01%2F2026&selected=7033726&PinnedHotelID=7033726&HadPinnedHotel=true&regionId=157359)

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...

7.8/10 Good! (1,000 reviews)

The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, ...

Reviewed on Dec 7, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true&regionId=157359)

[](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=12143&PinnedHotelID=12143&HadPinnedHotel=true&regionId=157359)

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

CA $228

CA $286 total

Dec 15 - Dec 16

includes taxes & fees

Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...

8.8/10 Excellent! (1,002 reviews)

Yes! Ease of registration! The staff helped us with dinning suggestions, hotel programs and amenities!

Reviewed on Dec 7, 2025

[](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=9679841&PinnedHotelID=9679841&HadPinnedHotel=true&regionId=157359)

[See all 4,687 properties in Shelter Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&regionId=157359)

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.

![Work and Play Special!  Extended Stay Discount ](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Work and Play Special! Extended Stay Discount 

 Shelter Island NY

Stay at this vacation home in Shelter Island. Enjoy free WiFi, private pools, and a garden. Popular attractions Wades Beach and Mashomack Preserve are located ...

10/10 Exceptional! (53 reviews)

This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want.

Reviewed on Nov 29, 2025

[](https://expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information)

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Montauk Manor

236 Edgemere St. Montauk NY

Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...

9/10 Wonderful! (1,265 reviews)

Staff was very nice and helpful! The gym was fantastic! Clean and well-equipped!

Reviewed on Nov 30, 2025

[](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

![Cliffside Resort Condominiums](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/1638a16b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Cliffside Resort Condominiums

61475 Route 48 (North Road) Greenport NY

Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...

8.8/10 Excellent! (249 reviews)

The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken.

Reviewed on Nov 12, 2025

[](https://expedia.ca/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

[See all properties in Shelter Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=157359&sort=VACATION_RENTAL)

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.

## Check Shelter Island hotel availability

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=2025-12-13&endDate=2025-12-14)[Dec 13 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=2025-12-13&endDate=2025-12-14)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=2025-12-14&endDate=2025-12-15)[Dec 14 - Dec 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=2025-12-14&endDate=2025-12-15)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=157359&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)

### Popular places to visit

#### Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries. 

[](https://expedia.ca/Gardiners-Bay-Country-Club-Shelter-Island.d6282173.Vacation-Attraction)

#### Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area. 

[](https://expedia.ca/Mashomack-Preserve-Shelter-Island.d6224462.Vacation-Attraction)

#### Shelter Island Historical Society

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums. 

[](https://expedia.ca/Shelter-Island-Historical-Society-Shelter-Island.d553248635961235094.Vacation-Attraction)

#### Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area. 

[](https://expedia.ca/Shelter-Island-Whales-Tail-Shelter-Island.d553248621554204762.Vacation-Attraction)

#### Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. 

[](https://expedia.ca/Shell-Beach-Shelter-Island.d553248621554204761.Vacation-Attraction)

#### Wades Beach

Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums. 

[](https://expedia.ca/Wades-Beach-Shelter-Island.d553248621554204759.Vacation-Attraction)

### Things to do

![The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC](https://mediaim.expedia.com/localexpert/330552/c1afebb8-4a31-47a1-af1e-6d13dd7d5c25.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

CA $247

per adult

**76%** of travellers recommend

[](https://expedia.ca/things-to-do/the-hamptons.a330552.activity-details)

[See all activities in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)

## Cities near Shelter Island

![East Hampton Main Beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252521-Long-Island.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### East Hampton

![Sag Harbor](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/252000/252775-Sag-Harbor.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Sag Harbor

![Photo by Benny Goh ](https://mediaim.expedia.com/destination/2/64a7a541b17dabdb743e9908dec5b467.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### East Marion

![Photo by Nina Dinoff](https://mediaim.expedia.com/destination/2/9a9f855657c0f02d64549df7b59e54eb.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Greenport West

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- [Visit Amagansett Lanes ](https://www.expedia.ca/Amagansett-Amagansett-Lanes.dx553248635976471387)
- [Visit Amagansett ](https://www.expedia.ca/Amagansett.dx73561)
- [Visit Bridgehampton ](https://www.expedia.ca/Bridgehampton.dx6130684)
- [Visit Coram ](https://www.expedia.ca/Coram.dx3000448254)
- [Visit Barnes Landing ](https://www.expedia.ca/East-Hampton-Barnes-Landing.dx553248635976472101)
- [Visit Clearwater Beach ](https://www.expedia.ca/East-Hampton-Clearwater-Beach.dx553248635976481631)
- [Visit East Hampton ](https://www.expedia.ca/East-Hampton.dx1524)
- [Visit East Marion ](https://www.expedia.ca/East-Marion.dx6069914)
- [Visit East Quogue ](https://www.expedia.ca/East-Quogue.dx6125932)
- [Visit Gordon Heights ](https://www.expedia.ca/Gordon-Heights.dx553248634999144533)
- [Visit Pipes Cove ](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
- [Visit Hampton Bays ](https://www.expedia.ca/Hampton-Bays.dx183681)
- [Visit Hamptons ](https://www.expedia.ca/Hamptons.dx6056452)
- [Kontokosta Winery ](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Visit Lion Head Beach ](https://www.expedia.ca/Lion-Head-Beach.dx553248635976395221)
- [Visit Mastic Beach ](https://www.expedia.ca/Mastic-Beach.dx6327542)
- [Visit Middle Island ](https://www.expedia.ca/Middle-Island.dx3000449083)
- [Visit Culloden Shores ](https://www.expedia.ca/Montauk-Culloden-Shores.dx553248635976472450)
- [Visit Montauk ](https://www.expedia.ca/Montauk.dx10637)
- [Visit Napeague ](https://www.expedia.ca/Napeague.dx553248634999149912)
- [Visit North Fork ](https://www.expedia.ca/North-Fork.dx553248635074841663)
- [Visit North Haven ](https://www.expedia.ca/North-Haven.dx553248634998589872)
- [Orient Vacations ](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides)
- [Visit Quogue ](https://www.expedia.ca/Quogue.dx183707)
- [Visit Bay Point ](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151)
- [Visit Sag Harbor ](https://www.expedia.ca/Sag-Harbor.dx154327)
- [Shelter Island Heights Vacations ](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)
- [Visit Shinnecock Hills ](https://www.expedia.ca/Shinnecock-Hills.dx553248634998586593)
- [Visit Shinnecock Reservation ](https://www.expedia.ca/Shinnecock-Reservation.dx553248634998728494)
- [Visit Southampton ](https://www.expedia.ca/Southampton.dx6782)
- [Visit Suffolk County ](https://www.expedia.ca/Suffolk-County.dx553248635083916458)
- [Visit Village of East Hampton ](https://www.expedia.ca/Village-Of-East-Hampton.dx553248634998945224)
- [Visit Wainscott Woods ](https://www.expedia.ca/Wainscott-Woods.dx553248635976471516)

- [Car rental Greenport ](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)

- [Things to do in Greenport ](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
- [Things to do in Shelter Island Heights ](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)

- Cities near Shelter Island
- Places of interest

[East Hampton](https://expedia.ca/East-Hampton.dx1524)[Sag Harbor](https://expedia.ca/Sag-Harbor.dx154327)[East Marion](https://expedia.ca/East-Marion.dx6069914)[North Haven](https://expedia.ca/North-Haven.dx553248634998589872)[Dering Harbor](https://expedia.ca/Dering-Harbor.dx553248634998885605)[Greenport West](https://expedia.ca/Greenport-West.dx553248635975876381)

- [Havens House ](https://expedia.ca/Havens-House-Shelter-Island.d6232745.Vacation-Attraction)
- [Cooper's Beach ](https://expedia.ca/Coopers-Beach-Southampton.d6326842.Vacation-Attraction)
- [Ocean Beach Park ](https://expedia.ca/Ocean-Beach-Park-New-London.d6071449.Vacation-Attraction)
- [Essex Steam Train ](https://expedia.ca/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction)
- [East Hampton Main Beach ](https://expedia.ca/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction)
- [Wolffer Estates Vineyard ](https://expedia.ca/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction)
- [Hither Hills State Park ](https://expedia.ca/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction)
- [Ditch Plains Beach ](https://expedia.ca/Ditch-Plains-Beach-Montauk.d6326860.Vacation-Attraction)
- [Kontokosta Winery ](https://expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
- [Lake Montauk ](https://expedia.ca/Lake-Montauk-Montauk.d553248621532665766.Vacation-Attraction)

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