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
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.
The Heights Hotel Deals
The Chequit
23 Grand Ave, Shelter Island Heights, NY
The price is AED 1,584 per night from May 14 to May 15
AED 1,584
AED 1,810 total
14 May - 15 May
includes taxes & fees
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 ...
"Excellent"
Reviewed on 10 November 2024
Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
The price is AED 768 per night from May 14 to May 15
AED 768
AED 946 total
14 May - 15 May
includes taxes & fees
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,000 reviews)
"I love this place. Next time I wish I could have a better view. I went there before the new rooms were added. Every time I went there, I stayed in the main building right upstairs from the check-in facing the water with my husband and I absolutely loved it. I was actually married there in the old ..."
Reviewed on 1 May 2025
Baron's Cove
31 West Water Street, Sag Harbor, NY
The price is AED 1,025 per night from May 22 to May 23
AED 1,025
AED 1,288 total
22 May - 23 May
includes taxes & fees
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (241 reviews)
"Beautiful, perfect location. Garden room was wonderful. Food amazing. Staff welcoming and friendly. Can’t wait to return!"
Reviewed on 11 May 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
The price is AED 320 per night from May 20 to May 21
AED 320
AED 367 total
20 May - 21 May
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. ...
7.6/10 Good! (955 reviews)
"Friendly staff at check in. Easy, convenient parking and modest room that is comfortable."
Reviewed on 3 May 2025
Sag Harbor Inn
45 West Water Street, Sag Harbor, NY
The price is AED 900 per night from May 14 to May 15
AED 900
AED 1,028 total
14 May - 15 May
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (517 reviews)
Great location, lovely staff
"Lovely hotel only a 10 min walk from the town centre. Staff were very friendly, the hotel itself had a gorgeous view across the water. Breakfast was adequate. I would recommend staying here."
Reviewed on 7 May 2025
The Bentley Hotel Southampton
161 Hills Station Rd, Southampton, NY
Fully refundable
The price is AED 584 per night from May 15 to May 16
AED 584
AED 667 total
15 May - 16 May
includes taxes & fees
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (259 reviews)
"Super cool looking. Clean and new. Spacious and comfortable!"
Reviewed on 11 May 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 neighborhoods around The Heights
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.
- Shelter Island Country Club
- Cooper's Beach
- The Hamptons Beaches
- East Hampton Main Beach
- Hammonasset Beach State Park
- Wolffer Estates Vineyard
- Hither Hills State Park
- Essex Steam Train
- Rocky Neck State Park
- Orient Point County Park
- Sag Harbor Marine Park
- Connecticut River
- 67 Steps Beach
- Shinnecock Hills Golf Course
- Harvey's Beach
- Kontokosta Winery
- Jamesport Vineyards
- Amagansett Beach
- Westbrook Town Beach
- The Jewish Center of the Hamptons
- Clinton Crossing Premium Outlets
- Shinnecock Nation Cultural Center and Museum
- Essex Island Marina
- Hole-in-the-Wall Beach
- Harbes Family Farm
- Orient Beach State Park
- Ponquogue Beach
- Georgica Beach
- Sunset Beach
- Macari Vineyards
- Pindar Vineyards
- Greenport Carousel