Where to stay on Shelter Island


The Chequit. (Credit: Skye Gillispie)

Sailing, shoreline walks and cocktails at Sunset Beach.

A Shelter Island getaway is one of the finest ways to spend your time away from home and the office. But those among us not lucky enough to have friends who own property with a guest cottage and dock rights are going to need a place to stay.

Luckily the inns and boutique hotels of Shelter Island provide attractive and homey accommodations.

From the recently reopened Shelter Island House to The Chequit, the Island’s hottest new inn, you can’t go wrong with a stay at these six properties.

Shelter Island House

Style: Sophisticated

R​ecently refurbished and located near Crescent Beach, The Shelter Island House has eight beachy rooms with garden views. The hotel offers a french bistro menu, p​étanque courts ​a​nd even f​ree use of bicycles.

Price:​ Summer rates start at $275 for a Queen Room

Perk:​ Refurbished petanque courts

11 Stearns Point Road
Shelter Island Heights
(631) 749-1633

Sunset Beach Hotel

Style: Trendy

E​njoy one of the 20 stylish guest rooms, all with their own private sun deck, water views, seating area and room service from the restaurant. ​All rooms provide a view of the picturesque Shelter Island sunset.

Price: S​ummer Rates start at around $430

Perk: ​Complimentary beach chair, umbrella and towels. Free bike and paddle board rentals

35 Shore Road
Shelter Island Heights
(631) 749-2001

Dering Harbor Inn

Style: Private

O​verlooking the harbor, the Dering Harbor Inn is an intimate place to get away. Stay in one of the inn’s waterfront villas or suites and enjoy its pool, tennis courts, dock and access to the gym at Shelter Island Yoga & Fitness. And it’s just a five minute walk to restaurants and shops.

Price: In-season ​rates start at $330 per evening for a studio

Perk:​ Heated pool overlooking the harbor

13 Winthrop Road
Shelter Island Heights
(631) 749-0900

The Pridwin Beach Hotel & Cottages

Style: Classic

G​o back in time at The Pridwin and its variety of accommodations. Stay in one of 40 hotel rooms or a cottage with a fireplace. The Pridwin has its own pool and there is a nearby beach lined with chaise lounge chairs. It also offers kayaks, sunfish and paddleboats for use on the bay. Stay on a Wednesday night and enjoy The Pridwin’s famous Wednesday night cookouts.

Perk:​ Water sports vehicles like kayaks, paddle boards and hydrobikes are available for rent

Price: S​ummer rates start at $279 during the week

81 Shore Road
Shelter Island
(631) 749-0476

The Chequit

Style: Modern classic

C​hances are if you’ve visited Shelter Island, you’ve laid eyes on the grand Chequit inn. Located in the heart of the island, this hotel offers a variety of restored rooms and suites and a magnificent porch. Amentities include the in-house White Hill Cafe ​as well as surf and skate shop Wampum. And check out the new year-round restaurant, Red Maple.

Perk: Complementary and daily changing breakfast menu

Price: S​ummer rates start at $195 for a double room

23 Grand Avenue
Shelter Island Heights
(631) 749-0018

The Ram's Head Inn. (Credit: Skye Gillispie)

The Ram’s Head Inn. (Credit: Skye Gillispie)

Ram’s Head Inn

Style: Traditional

T​ake pleasure in a unique experience at the serene Ram’s Head Inn. Stay in one of 17 rooms, in either a private bath, shared bath or two bedroom suite. Enjoy fine dining with a view of the harbor at the inn’s seasonably ­focused restaurant. There are also on-site tennis courts, sailboats, kayaks and paddle boards which are all complementary for guests.

Perk:​ Complementary waterfront yoga classes every weekend

Price: S​ummer rates range from $150 per night for shared bath on weekdays to $425 per night for two bedroom suite on weekends

108 South Ram Island Drive
Shelter Island Heights
(631) 749-0811