A look at the outdoor igloos at Gurney's in Montauk.

A look at the outdoor igloos at Gurney's in Montauk. Credit: Randee Daddona

A summer getaway to the East End doesn't have to be booked at summer prices. Several Long Island hotels are rolling out holiday promotions and Black Friday sales that let travelers lock in discounted room rates now for stays extending well into 2027.

The deals include up to 50% off at an oceanfront Montauk resort, plus 30% savings at two boutique properties in Greenport and Montauk. Whether you're planning a beach vacation for next summer, a weekend exploring North Fork wineries or a quieter offseason escape, booking during the holiday sales could mean more room in the budget for dining, activities and other stops along the way.

Gurney’s Montauk Resort

290 Old Montauk Hwy., Montauk

  • Savings: 30% off rooms, 40% off suites and 50% off cottages and residences.
  • Booking window: Nov. 9-Dec. 1
  • Travel window: Nov. 9-Oct. 31, 2027
The indoor pool at Gurney's Montauk.

The indoor pool at Gurney's Montauk. Credit: Gurney’s Montauk

Gurney’s Montauk Resort is offering some of its biggest savings of the year across its oceanfront accommodations, with discounts on rooms, suites, cottages and residences. The deal covers stays through Oct. 31, 2027, making it an opportunity to lock in lower rates for next summer's beach season.

There are also reasons to visit during the colder months. The resort's heated igloos, inspired by Gurney’s upcoming Lake Tahoe property, are available through April 4, 2027. Guests can also take advantage of Sunset Hour at Gigi’s Bar, with discounted drinks and bites Sundays through Thursdays, and weekly movie nights in the spa on Fridays and Saturdays.

MORE INFO gurneysresorts.com; 631-668-2345

Oyster Estate

326 Front St., Greenport

  • Savings: 30% off
  • Booking window: Nov. 17-Dec. 3.
  • Travel window: Through Dec. 30, 2027
A look inside one of the 34 redesigned guest rooms...

A look inside one of the 34 redesigned guest rooms at Oyster Estate in Greenport. Credit: Matt Kisiday

Oyster Estate is a newly reimagined, 34-room boutique hotel in the heart of Greenport Village that opened in September. The property blends design inspired by the North Fork's historic harbor, farms and vineyards, using custom millwork and original artwork throughout. A newly built courtyard pool and patio serve as the hotel's centerpiece, while Fortune Favors, an Asian-inspired cocktail bar, restaurant and listening room, debuted in October. It offers an intimate, grounded coastal retreat within walking distance of local shops, vineyards and working docks.

MORE INFO oysterestate.com; 833-767-4681

Hotel Corduroy

540 West Lake Dr., Montauk

  • Savings: 30% off
  • Booking window: Nov. 17-Dec. 3.
  • Travel window: Through Dec. 30, 2027
One of the 29 redesigned guest rooms at Hotel Corduroy...

One of the 29 redesigned guest rooms at Hotel Corduroy in Montauk. Credit: Matt Kisiday

Formerly the Sunset Montauk, Hotel Corduroy is a 29-room boutique hotel that opened in May after a renovation that reimagined the 1980s-era motel into a modern coastal getaway. The property features refreshed guest rooms, a shared outdoor gathering space with firepits and sunset views, and access to beach gear, bicycles and a private beach area. It's also steps from Sunset Beach and the marina, making it a convenient home base for a summer trip.

MORE INFO thehotelcorduroy.com; 855-525-9757

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