Name: The Bentley Hotel Southampton
Price range: $160 total
Rating: 9.6

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.

See our Where To Stay guide

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$541 nightly

$618 total

Apr 20 - Apr 21

Total with taxes and fees

Book a stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Popular attractions Hither Woods Preserve and Hither ...

8.4/10 Very Good! (754 reviews)

Our family of four stayed for 3 nights in a two bedroom suite with ocean views. We booked it last minute for spring break. Overall, we had an amazing time and enjoyed our stay despite the cold temps. The room was clean. I saw no obvious signs of aging of furniture, fittings and walls - a huge plus ...

Reviewed on Apr 14, 2026

Montauk Manor

236 Edgemere St. Montauk NY

$168 nightly

$192 total

Apr 20 - Apr 21

Total with taxes and fees

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 ...

9.2/10 Wonderful! (1,324 reviews)

The kitchen was perfect, only thing missing was utensils. There is a local store on the way to the manor to pick some of those staples up from.

Reviewed on Apr 13, 2026

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

$140 nightly

$160 total

Apr 26 - Apr 27

Total with taxes and fees

Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...

9.6/10 Exceptional! (463 reviews)

The hotel is clean

Reviewed on Apr 16, 2026

See all 4,767 properties in Shelter Island Heights

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 ...

9.2/10 Wonderful! (1,324 reviews)

The kitchen was perfect, only thing missing was utensils. There is a local store on the way to the manor to pick some of those staples up from.

Reviewed on Apr 13, 2026

North Fork Cottages & RV Resort

690 Queen St Greenport NY

Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...

Windward Shores Ocean Resort

2062 Montauk Highway Amagansett NY

Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...

8.8/10 Excellent! (310 reviews)

When I went to the property it was not shoveled. A challenge to get to the room. I enjoyed the room with minor things that could change.

Reviewed on Mar 2, 2026

See all properties in Shelter Island Heights

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.

Check Shelter Island Heights hotel availability

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.