These East End hotels are just as delightful in the cooler months
The East End of Long Island has long been renowned as a tranquil retreat, offering ample opportunity for rest and relaxation amidst its picturesque landscapes and coastal charm. As of the last few years, many of the region’s historic properties have been renovated and refreshed, making it a great time to come check them out. When it comes to planning, summer is the busiest time of year for visitors, resulting in the highest accommodation prices. For those seeking a more serene and affordable experience, the fall is as an ideal time to visit.
LDV At the Maidstone
An East Hampton landmark, the historic Maidstone Inn recently reopened under new ownership by LDV Hospitality, who aim to infuse “a touch of la dolce vita” to the Hamptons through an Italian-centric food and beverage program. The hotel underwent a comprehensive makeover, featuring a lavish renovation of the lobby and rejuvenated guest rooms. Originally constructed over 150 years ago, the building served as both a tannery and lodge in its early days. Rates start at $565 in October and November (versus over $1,000 a night in September and the summer).
207 Main St., East Hampton; 631-324-5006; themaidstone.com
Canoe Place Inn
The historic Canoe Place Inn reopened in 2023 after being closed for nearly two decades. Originally rebuilt in 1920 after a fire, the property was renovated to include updated guestrooms, suites and cottages as well as a new restaurant, spa and event space. Weekend rates start at $350 in the fall (half the average rate of $700 in the summer).
239 East Montauk Highway, Hampton Bays; 631-763-6300; canoeplace.com
The Pridwin Hotel and Cottages
The Pridwin has welcomed guests on Shelter Island since 1927, and completed a full renovation in 2022, where the entire nearly 10-acre property was refreshed with the goal of enhancing the natural charm of the property while fortifying it for longevity. Sweeping water views and a grand manicured lawn adorned with Adirondack chairs are what set this hotel apart from others. Weekend rates in the fall start at $403 a night (versus an average of $900 a night in the summer).
81 Shore Road, Shelter Island; 631-749-0476; caperesorts.com/pridwin
The Chequit
An extensive renovation was completed in 2022, which was also the 150-year anniversary of the building itself. The Chequit’s reopening brought new fine dining options, including a restaurant, tavern and cafe. In addition to the enhanced dining options, guests can also book pre-arranged wine tours through the hotel. Average room rates start at $350 in the fall, a significant decrease from the summer season.
23 Grand Ave., Shelter Island Heights; 631-749-0018; thechequithotel.com
The Shoals
Once a historic working marina, the Shoals, which opened in 2022, is situated dockside overlooking the Peconic Bay and Shelter Island. Unique to this hotel, or “boatel” as its also called, is that it can be accessed by land or sea, with 20 slips available in addition to the 20 suites the hotel offers. Room rates vary throughout the fall but will decrease by November.
61600 Main Road, Southold; 631-765-5121; theshoalsnorthfork.com
Sound View
Once a 10-room motel that opened in 1953, the Sound View is now a fully renovated 55-room hotel with breathtaking views of the Long Island Sound. The on-site restaurant, the Halyard, not only features delectable local seafood, but is also a great spot to catch the sunset. Rates for a fall weekend start around $583 a night (versus $879 in the summer).
58775 Route 48, Greenport; 631-477-1910; soundviewgreenport.com
Silver Sands Motel & Beach Bungalows
A North Fork staple since 1957, the motel reopened in the summer of 2023 after an extensive renovation to update and modernize the property, all while keeping the overall sense of nostalgia in place. Unique amenities include a private beach, a 1950s-inspired diner and tours of the surrounding oyster farm. In addition to the motel rooms, bungalows and beach houses are also available to rent. Motel rooms start at $200 a night in the fall (versus $470 a night in the summer).
1400 Silvermere Road, Greenport; 631-997-1957; silversandsmotel.com
Montauk Yacht Club
Originally built in 1928, the Montauk Yacht Club recently underwent a thorough renovation, most notably adding their new restaurant Ocean Club Montauk. The hotel also refreshed its common areas, accommodations and outdoor spaces, adding a state-of-the-art gym and a full-service spa. The 35-acre property is home to the largest marina in the Hamptons, allowing for plenty of different outdoor and water activities for its guests. Rates start at around $458 per night in October and November and allow for one-night bookings (versus September and summer, which typically have three-night minimums and comes at a more premium cost).
32 Star Island Road, Montauk; 631-668-3100; montaukyachtclub.com
Hotel Moraine
Previously the Sunset Motel, Hotel Moraine opened its doors in June 2023 following a full renovation, including the addition of a pool and creation of a “clubhouse” that is used for happy hours, private events or a space to play games and watch a movie. September weekend rates start at $775 per night, and October weekend rates start at $575 per night (versus the $850 starting rate in the summer).
62005 Route 48, Greenport; 631-477-1776; hotelmoraine.com
Seven Beach Lane
Aptly named after the address of the property, Seven Beach Lane is a fully renovated, 16-room boutique hotel where “historic charm meets modern luxury”. The building itself, a Victorian built in 1885, was most recently the Grassmere Inn before reopening this past summer as the new luxury hotel. Amenities include both indoor and outdoor dining, fitness classes, a heated saltwater pool, an outdoor sauna and a cold plunge. In its inaugural year, special pricing will be offered starting at $749 a night on weekends.
7 Beach Lane, Westhampton; 631-684-0777; sevenbeachlane.com
