Shelter Island Hotels – Getaway to your best stay!
Once you discover Shelter Island, you will definitely want to stay awhile. Since the Island is small, there are only a handful of Shelter Island Hotels, many of which also have excellent restaurants. Therefore, remember to BOOK EARLY – especially on July 4th and other holiday weekends. In addition, summer season is always more expensive than off-season and that is reflected in pricing. Most of these hotels stay open year-round, available for cozy winter retreats. Read on for some of my favorite picks in wonderful Shelter Island.
Sunset Beach Hotel
Escape to Sunset and you’ll feel like you’re waking up in a different world with a beachy casual-chic attitude. Feel a European vibe in this unique, charming hotel located on Crescent Beach. Enjoy complimentary beach chairs, towels, and bicycles. Play petanque and pingpong. Moreover, you will find paddle board rentals and a massage tent for an excellent massage on the beach.
Sunset Beach Hotel has a terrific outdoor lounge area with a fire pit and DJ. The three-level restaurant and bar area are always filled with a lively crowd. Rosé wine is flowing and a Frosé is perfect on a hot summer day. Large, clean studio rooms all have spacious sundecks facing the bay. Decor is minimalist with a large closet but could use a place to put folded clothing. Being right on the beach makes this the ultimate spot with a French twist.
The Pridwin Hotel
The Pridwin reminds me of a grand hotel, classic and timeless. BONUS- it was just completely renovated and is beautiful. It has a huge lobby, very nice rooms and a beautiful new pool. In addition, the balcony has one of the best dining views on the island, with delicious. It is a short 10 min walk to Sunset Beach Hotel, which is a hot spot both day and night. Not only can you get rooms in the main building, but there are also cottages with private decks and fireplaces.
The Chequit Hotel
The totally renovated Chequit Hotel is now a beautiful a terrific option on Shelter Island. You are right in the village. The grounds and rooms are absolutely beautiful! Moreover you can walk to the North Ferry then continue directly into Greenport. You are not on the beach, but they will have ebike rentals-check on that if you book. This is definitely a great option.
Shelter Island House 
You will discover casual sophistication and a chance to explore the local feel without sacrificing luxury. The hotel has both a lounge bar and an outdoor bar in the garden, plus indoor and outdoor dining with a brasserie style menu that has a sophisticated feel.Shelter Island House has a pool and is close to Crescent Beach. The property just opened a delicious new restaurant, Caci.
West Neck Guest House
West Neck Guesthouse, is another option on the island. The property offers comfy and appointed guest rooms all with king beds, private baths, flat screen TV’s with cable, and Wi-Fi. Just a 10 minute walk from Crescent Beach.