Shoulder season prices make the fall a great time to check out some of the East End’s recently renovated hotel gems
For centuries, the East End of Long Island has been renowned as a tranquil retreat, offering ample opportunity for rest and relaxation amid picturesque landscapes and coastal calm — and many of the hotels that have long welcomed visitors still do. Over the last few years, though, many of these historic properties have been renovated and refreshed, finding the balance between old charm and modern amenities. If you’ve been curious to check out some of your old faves, the days and weeks following Tumbleweed Tuesday are good bet. 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.
The Maidstone 207 Main St., East Hampton; 631-324-5006
An East Hampton landmark, the Maidstone recently reopened under new ownership by LDV Hospitality, who aim to bring “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/November (vs. over $1,000/night in September and during the summer).
The Pridwin Hotel & Cottages 81 Shore Road, Shelter Island; 631-749-0476
The Pridwin has welcomed guests on Shelter Island since 1927, and completed a full renovation in 2022, when the nearly 10-acre property was entirely refreshed with the dual goal of enhancing its natural charm and fortifying it for longevity. Sweeping water views and a grand manicured lawn dotted with Adirondack chairs set this hotel apart from others. New extras include an on-premises spa, yoga on the lawn and an excellent cocktail program — along with all the classic board games, biking and spectacular sunsets you’ve come to expect. Weekend rates in the fall start at $403/night (vs. a summer average of $900/night).
Canoe Place Inn 239 East Montauk Highway, Hampton Bays; 631-763-6300
The historic Canoe Place Inn reopened in 2022 after being closed for nearly two decades. Originally rebuilt in 1920 after a fire, the property was renovated to include updated guest rooms, suites and cottages as well as a new restaurant, spa and event space, and has a robust entertainment schedule with everything from celebrity-led talks to comedy and music, as well as curated beach experiences (hey, fall is the best time on the sand!) and paddleboarding and kayaking excursions. Weekend rates start at $350 in the fall (vs. an average of $700 in high season).
The Chequit 23 Grand Ave., Shelter Island Heights; 631-749-0018
An extensive renovation was completed in 2022, which was also the 150-year anniversary of the structure itself. The reopening brought new fine dining options, including a restaurant, popular tavern and porch-side café, along with outdoor firepits for cozy fall gatherings. In addition to the enhanced dining options, guests can book pre-arranged wine tours through The Chequit. Average fall room rates start at $350, a significant savings from the summer season.
Hotel Moraine 62005 Country Road 58, Greenport; 631-477-1776
Formerly the Sunset Hotel, Hotel Moraine opened its doors in June 2023 following a full reconstruction, including the addition of a pool and creation of a “clubhouse” used for happy hours, private events or a space to play games and watch a movie. September weekend rates start at $775/night, and October weekend rates start at $575/night (vs. an $850 starting rate in the summer).
The Shoals 61600 Main Road, Southold; 631-765-5121
Once a historic working marina, the Shoals, which opened in 2022, is situated dockside overlooking Peconic Bay and Shelter Island. Unique to this hotel — or “boatel,” as it’s also called — is accessibility by land or sea, with 20 slips available in addition to it’s 20 suites. Room rates vary throughout the fall but look for the best values around November.
Montauk Yacht Club 32 Star Island Road, Montauk; 631-668-3100
Built in 1928, Montauk Yacht Club recently underwent a thorough renovation, most notably adding its new restaurant, Ocean Club Montauk. The hotel also refreshed its common areas, rooms and outdoor spaces, and added a state-of-the-art gym and full-service spa. The 35-acre property is home to the largest marina in the Hamptons, giving guests access to plenty of varied outdoor and water activities. Rates start at around $458/night in October/November and single-night bookings are accepted. (During the summer and September, there is typically a three-night minimum and prices are more premium.) .
Silver Sands Motel & Beach Bungalows 1400 Silvermere Road, Greenport; 631-997-1957
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/night in the fall (vs. $470/night in the summer).
Sound View 58775 County Road 48, Greenport; 631-477-1910
Once a sleepy, 10-room motel that opened in 1953, the Sound View is now a fully renovated 55-t room hotel with breathtaking views of 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 begin at about $583/night (vs. $879 in the summer).
Seven Beach Lane 7 Beach Lane, Westhampton; 631-684-0777
Seven Beach Lane is a fully renovated, 16-room boutique hotel where “historic charm meets modern luxury.” The building itself, a Victorian dating to 1885, was most recently the Grassmere Inn, and reopened this past summer as a luxury hotel with a midcentury modern vibe. Amenities include both indoor and outdoor dining with lots of local sourcing, 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/night on weekends (pricey, yes, but it’s slotted to go up next summer — forewarned is forebooked!).
