5/5 - Excellent
Verified traveler
Very serene and quiet.
Shelter Island Heights, NY
Travel Guide
Visit Shelter Island Heights
Where to stay in Shelter Island Heights
The Heights
4.5/5(10 area reviews)
If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.
The Pridwin Hotel
81 Shore Road Shelter Island Heights NY
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (84 reviews)
Overall the places is nice, clean and great views
Reviewed on Oct 21, 2025
The Chequit
23 Grand Ave Shelter Island Heights NY
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.
Reviewed on Oct 10, 2025
Shelter Island House
11 Stearns Point Rd Shelter Island Heights NY
Book a stay at this golf hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sunset Beach and Shelter Island ...
8.2/10 Very Good! (57 reviews)
Great Shelter Island Hotel
One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try.
Reviewed on Oct 24, 2025
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.
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
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
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Sag Harbor NY
Book a stay at this family-friendly vacation home in Sagaponack. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in ...
10/10 Exceptional! (87 reviews)
Property was very responsible and amazing to work with!!
Reviewed on Sep 29, 2025
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.
Popular places to visit
Sunset Beach
4.5/5(9 reviews)
Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Crescent Beach
4.5/5(4 reviews)
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
Sylvester Manor
You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
$179
per adult
76% of travellers recommend
Reviews of Shelter Island Heights
4.7
Top Destination
5/5 - Excellent
Verified traveler
love the island and the local very friendly will go back but not stay at the pridwin, we did eat dinner there was very disappointing food was dry and overdone
5/5 - Excellent
Verified traveler
We loved the area, the people, the food, the ferry. We came to celebrate our anniversary and we will be back.
5/5 - Excellent
Jennifer
Wonderful, peaceful place to visit. Easy to get to from NYC. I'd go back in a heartbeat.
5/5 - Excellent
Phil
Over rated and expensive
Explore a world of travel with Expedia
- Hotels near The Heights
- Hotels near Shelter Island Country Club
- Greenport Hotels
- Hotels near Sunset Beach
- Hotels near Sylvester Manor
- Hotels near Pipes Cove
- Shelter Island Hotels
- Hotels near Greenport Station
- Hotels near East End Seaport Maritime Museum
- Hotels near Railroad Museum of Long Island
- Hotels near Crescent Beach
- Hotels near Greenport Carousel
- Hotels near Camera Obscura
- Resorts & Hotels with Spas in Greenport
- B&B in Greenport
- Beach Hotels in Greenport
- Family Hotels in Greenport
- Oceanfront Hotels in Greenport
- Hotels near Shelter Island Whale's Tail
- Winery Hotels in Greenport
- Boutique Hotels in Greenport
- Hotels with a Pool in Greenport
- 5 Star Hotels in Greenport
- Hilton Hotels in Greenport
- Cheap Hotels in Greenport
- Cottages in Greenport
- Condo Rentals in Greenport
- Romantic Hotels in Greenport
- Hotel Wedding Venues Hotels in Greenport
- Motels in Greenport
- 4 Star Hotels in Greenport
- Hotels with Fireplaces in Greenport
- Hotels with Bars in Greenport
- Adults Only Resorts & in Greenport
- Historic Hotels in Greenport
- Apartments in Greenport
- Cabin Rentals in Greenport
- Luxury Hotels in Greenport
- Hotels with Hot Tubs in Greenport
- Hotels with Free Parking in Greenport
- 3 Star Hotels in Greenport
- Wyndham Hotels in Greenport
- Hotels with Tennis Courts in Greenport
- Hotels with Restaurants in Greenport
- Hotels with a Gym in Greenport
- Houseboats in Greenport
- Golf Hotels in Greenport
- Gay friendly Hotels in Greenport
- Hotels with Kitchenettes in Greenport
- Business Hotels in Greenport
- Hotels with Balconies in Greenport
- Farmstay in Greenport
- Resorts in Greenport
- Vacation Homes in Greenport
- Hotels & Resorts for Couples in Greenport
- Hotels with Room Service in Greenport
- Hotels near Greenport Farmers' Market
- Resorts in Shelter Island
- B&B in Shelter Island
- Houseboats in Shelter Island
- Cottages in Shelter Island
- Cabin Rentals in Shelter Island
- Vacation Homes in Shelter Island
- Resorts & Hotels with Spas in Shelter Island
- Apartments in Shelter Island
- 4 Star Hotels in Shelter Island
- 5 Star Hotels in Shelter Island
- Hotels with Hot Tubs in Shelter Island
- Golf Hotels in Shelter Island
- Hotels with a Pool in Shelter Island
- Luxury Hotels in Shelter Island
- Villas in Shelter Island
- Condo Rentals in Shelter Island
- Sunset Beach
- Crescent Beach
- Shelter Island Country Club
- Sylvester Manor
- Menhadden Lane Beach
- Cooper's Beach
- Ocean Beach Park
- Hammonasset Beach State Park
- Essex Steam Train
- East Hampton Main Beach
- Wolffer Estates Vineyard
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Orient Point County Park
- Connecticut River
- Raphael Winery
- Clinton Crossing Premium Outlets
- Ditch Plains Beach
- 67 Steps Beach
- Guild Hall
- Lake Montauk
- Macari Vineyards
- Westbrook Town Beach
- Kontokosta Winery
- Jamesport Vineyards
- Mitchell College
- Harvey's Beach
- South Edison Beach
- Pindar Vineyards
- LongHouse Reserve
