Visit The Heights
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.
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 Wi-Fi, free parking and premium bedding. Popular attractions Shelter Island Country Club and ...
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.
Reviewed on 10 Oct 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.8/10 Good! (1,002 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...
Reviewed on 3 Nov 2025
Sound View Greenport
58775 County Rd 48, Greenport, NY
Fully refundable
The price is 5.129.027 ₫ per night from 15 Dec to 16 Dec
5.129.027 ₫
7.149.482 ₫ total
15 Dec - 16 Dec
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (588 reviews)
Beautiful and unique property. We really enjoyed our weekend getaway
Reviewed on 13 Nov 2025
Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
The price is 2.665.303 ₫ per night from 23 Nov to 24 Nov
2.665.303 ₫
3.065.098 ₫ total
23 Nov - 24 Nov
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,003 reviews)
Clean place, nice staff
Reviewed on 11 Nov 2025
The Atlantic Hotel
1655 County Road 39, Southampton, NY
Stay at this hotel in Southampton. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
7/10 Good! (965 reviews)
Clean room. Courteous staff
Reviewed on 29 Oct 2025
Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
The price is 6.379.335 ₫ per night from 30 Nov to 1 Dec
6.379.335 ₫
7.995.117 ₫ total
30 Nov - 1 Dec
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,001 reviews)
amenities clean room with turndown service
Reviewed on 14 Nov 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.
The Heights Travel Guide
- Cooper's Beach
- Essex Steam Train
- Hammonasset Beach State Park
- Orient Point County Park
- Shinnecock Hills Golf Course
- Hither Hills State Park
- Connecticut River
- Clinton Crossing Premium Outlets
- Raphael Winery
- Kontokosta Winery
- Guild Hall
- Macari Vineyards
- 67 Steps Beach
- Harvey's Beach
- Pindar Vineyards
- Pollock-Krasner House and Study Center
- Sunset Beach
- Parrish Art Museum
- Shinnecock Nation Cultural Center and Museum
- Pleasure Beach
- Bedell Cellars
