Popular places to visit
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.
Sunset Beach
Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Crescent Beach
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
Things to do
Long Island Wine and Food Day Trip with Sommelier host from NYC
RM625
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
RM626
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
RM588
per adult
Top hotels in The Heights
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 Aug 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is RM338 per night from 14 Sept to 15 Sept
RM338
RM389 total
14 Sept - 15 Sept
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! (1,000 reviews)
"Pros: Decent basic accommodation with restaurants and stores nearby. Friendly staff. Great outdoor area in back of inn. Cons: need light blanket or two in room. Bedspreads are too hot! Overall, we enjoyed our stay here."
Reviewed on 8 Sep 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (929 reviews)
"Very nice staff and great location"
Reviewed on 7 Sep 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is RM1,505 per night from 24 Sept to 25 Sept
RM1,505
RM1,836 total
24 Sept - 25 Sept
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,008 reviews)
"My fiancé and I recently spent a few nights at this beautiful hotel by the water in Old Saybrook, and we couldn’t have asked for a more perfect getaway. From start to finish, everything was exceptional. The cleanliness throughout the property was flawless — every space felt fresh, spotless, and well ..."
Reviewed on 9 Sep 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
The price is RM1,222 per night from 29 Sept to 30 Sept
RM1,222
RM1,603 total
29 Sept - 30 Sept
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (566 reviews)
Wonderful but the bathroom is too small
"We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due ..."
Reviewed on 7 Sep 2025
The Harbor Front Inn
209 Front St, Greenport, NY
The price is RM822 per night from 13 Oct to 14 Oct
RM822
RM1,145 total
13 Oct - 14 Oct
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (515 reviews)
"Great location ,beautiful hotel,nice staff"
Reviewed on 25 Aug 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.
Other neighbourhoods around The Heights
Hay Beach
When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.
