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.
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.
The Pridwin Hotel
81 Shore Road, Shelter Island Heights, NY
Stay at this 4-star 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! (77 reviews)
"Shelter Island is definitely a gem"
Reviewed on 11 September 2025
The Chequit
23 Grand Ave, Shelter Island Heights, NY
Stay at this 3-star hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and ...
8.8/10 Excellent! (36 reviews)
"Always a sold stay on Shelter Island"
Reviewed on 23 August 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is AED 294 per night from Sep 22 to Sep 23
AED 294
AED 338 total
22 Sep - 23 Sep
includes taxes & fees
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! (1,008 reviews)
"We were in town for a party. Very convenient location and friendly staff."
Reviewed on 14 September 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 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,248 reviews)
"Clean spacious room. Friendly staff. Excellent onsite restaurant"
Reviewed on 12 September 2025
Windward Shores Ocean Resort
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (294 reviews)
"Very nice & affordable"
Reviewed on 2 September 2025
Montauk Oceanside Suites
115 South Emerson Avenue, Montauk, NY
Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...
8.4/10 Very Good! (414 reviews)
"Property was clean and nice but did not smell good inside, it need candles and air freshener, also think something was off about the sewage system"
Reviewed on 16 September 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
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
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.
Shelter Island Country Club
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
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
- Sunset Beach
- Crescent Beach
- Shelter Island Country Club
- Sylvester Manor
- Menhadden Lane Beach
- The Hamptons Beaches
- Ocean Beach Park
- Cooper's Beach
- Hammonasset Beach State Park
- East Hampton Main Beach
- Essex Steam Train
- Wolffer Estates Vineyard
- Orient Point County Park
- Hither Hills State Park
- Ditch Plains Beach
- Kontokosta Winery
- Connecticut River
- 67 Steps Beach
- Shinnecock Hills Golf Course
- Harvey's Beach
- Clinton Crossing Premium Outlets
- Sag Harbor Marine Park
- Rocky Neck State Park
- Macari Vineyards
- Pindar Vineyards
- Raphael Winery
- Harkness Memorial State Park
- Lake Montauk
- The Jewish Center of the Hamptons
- Shinnecock Nation Cultural Center and Museum
- Hole-in-the-Wall Beach
- Harbes Family Farm
