The Chequit

Restored Victorian architecture with views over Long Island Sound anchors The Chequit in Shelter Island Heights, a 4-star property rated 9.0 on Booking.com. Each air-conditioned room includes premium bedding, a private bathroom, and free toiletries; family rooms with daybeds for children are available. The on-site restaurant, Red Maple, serves seasonal food from a bar and expanded terrace for open-air dining during summer. A complimentary breakfast features fresh fruits, pastries, and homemade items. Free WiFi and free private parking are provided, and the inn offers a shared lounge, sun terrace, and outdoor furniture. A fleet of reconditioned vintage bikes is available for complimentary island exploration. The Chequit is pet-friendly and provides concierge service, daily housekeeping, luggage storage, and private check-in/check-out. Its location near the North Ferry allows easy access from the mainland, with Montauk 34 km away and East Hampton 20 km away. The interior decor draws on 1940s glamour, and a British-style pub atmosphere complements the raw bar offering local oysters and clams.

Lovingly restored Victorian building with views over Long Island Sound

Complimentary breakfast with fresh fruits, pastries, and homemade items

Fleet of vintage bikes provided free of charge for island exploration

On-site Red Maple restaurant features seasonal food and a raw bar with local shellfish

Coffee not available in the room or lobby; guests receive a coupon for a nearby establishment

Tuesday nights feature DJ music that may disturb light sleepers (not always disclosed at booking)