If you are looking for Long Island hotels for any reason, the low season (read winter) is perhaps the best time to take advantage of the slower pace on The Island. The low season brings great deals, thinning crowds and plenty of opportunities for relaxation and rejuvenation, be it close to New York City in Nassau County or as far on The Island as you can go, The East End amidst all of the beautiful farms and North Fork Wineries.
Nassau County, Long Island Hotels
Garden City Hotel
If you are looking for a classic hotel that’s been updated with a ton of chic style in the heart of Nassau County, then you should check out the hotel in my hometown of Garden City. The famous Garden City Hotel is looking fantastic these days after a recent (and seemingly ongoing) multi-million dollar renovation and improvement effort. New rooms, new restaurants, and a new vibe really speaks to the quality of this place.
Stay at the Garden City Hotel and upon check-in receive a winter-inspired amenity, signature cocktails by the fire place in King Bar and Continental Breakfast for 2.
Relax and enjoy Mynd Spa & Salon, take a dip in the heated indoor pool or just lounge all day in your deluxe room accommodations. If you prefer to take a stroll down 7th street, you can enjoy all the local boutiques, restaurants and history that Garden City has to offer.
Rate: $249 per night plus applicable taxes
Room Type: Deluxe King or Double
Booking Dates: January 7, 2020 – March 31, 2020
Travel Dates: January 7, 2020 – March 31, 2020
Inn at Fox Hollow
The Anthony Scotto Dinner Package is a pretty awesome way to get the most out of your stay in the area. The Scotto family has been creating great food and memories on the Island for decades. Anthony Scotto has really upped the game with his amazing line-up of high quality, ultra trendy North Shore spots.
Includes an overnight Stay & $150 Gift Card toward dinner at RARE650, Blackstone Steakhouse or One North. This are Long Island’s Premier Restaurants located just minutes from the hotel. It also include shuttle service there and back upon request and reservations if possible. It also include a full American Breakfast at the hotel the next morning. Located at 7755 Jericho Turnpike, Woodbury, LI, New York, 11797; 516-224-8100; www.thefoxhollow.com/hotel
South Fork, Long Island Hotels
Baker House 1650
East Hampton’s casually elegant Baker House 1650 is offering several winter packages, including the Winter Wine Experience, which starts on arrival with a gift bag and two mini bottles of Moet Chandon Rose Champagne delivered to your room.
A wonderful part of this for me is that it includes something from our amazing Long Island wineries. Have a tasting at the gorgeous and impressive Wolffer Estate (transportation included), as well as a $100 dining credit at a list of the inn’s favorite in-town restaurants. A late checkout, at 1 p.m., allows you to sleep in. Located at 181 Main St., East Hampton; 631-324-4081; bakerhouse1650.com
Baron’s Cove is new and amazing, with views of the harbor. There’s a distinct country yet nautical feel to the place, with it’s porch and rockers. While it may be a little bit country, it’s luxury all the way with beautiful decor, spa, and all that you expect from a luxury hotel.
The amazing downtown Sag Harbor, which some say is the best on the East End, is packed with restaurants, galleries, and more. This is also a locals-based, year-round town. The Winter Warm-up Package includes a restaurant dining credit, complimentary hot chocolate with whipped cream, late checkout at 1 p.m., and 15% off spa services. Located at 31 W. Water St., Sag Harbor; 844-227-6672; caperesorts.com/barons-cove
Gurney’s has gone from simple Montauk hotel to a luxury powerhouse. While the Yacht Club and Newport, RI locations are fantastic, this location is stunning. Everything is top notch and brand new, from the rooms to the many eating and drinking spots.
Be sure to check out the famous spa at Gurney’s. We’re talking Finnish rock sauna, Russian steam room, and indoor seawater pool! The Winter Weekend Hygge Package includes a $100 resort credit, in-room DIY hot toddies, a Gurney’s winter blanket and a late 2 p.m. checkout. Located at 290 Old Montauk Hwy., Montauk; 631-668-2345; gurneysresorts.com
North Fork, Long Island Hotels
South Harbor Inn
the North Fork’s newest luxury B&B is called the South Harbor Inn. It’s a wonderfully renovated 1897 farmhouse with just four beautiful, classic rooms feature fireplaces and Frette linens. Breakfast is all North Fork, sourced from local farms. Ask your hosts to arrange a wine tour to really get the most of your stay.
The Cozy Winter Escape package includes a two-night stay in a room with a fireplace, two Frette bathrobes to take home and two classic flights at the Shinn Estate Winery, for $489 a night. Located at 565 S. Harbor Rd., Southold; 646-552-5047; southharborinn.com
The Menhaden is an amazing hotel on the water in Greenport Village. Rooms have Restoration Hardware Furnishings. Each floor offers local snacks and ice cream complimentary. There’s even an electric-powered Moke available to drive around town.
Be sure to check out s’mores around the rooftop fire pit, creating your own gin or aquavit at Matchbook Distilling, and a barrel cellar tour at Macari Wines. During the winter months, the hotel is offering 15% off weekend rates . Located at 207 Front St., Greenport; 631-333-2777; themenhaden.com
The Sound View Hotel
The Sound View Hotel is a really cool funky, yet comfy motel in Greenport. The LI Sound views are amazing. The restaurant, the Halyard, and a hip piano bar, are amazing places to hang out.
The motel is offering 30% off their best available rate for December and January, with a two-night minimum stay. Visit nearby North Fork wineries, sample local oysters at Little Creek Oyster Farm or just enjoy the sound of the waves crashing. Greenport Village is 5 minutes away and packed with all the restaurants, bars, boutiques and more you could hope for. It’s the hub of the North Fork food and drink scene. It’s also close to the soon-to-be reopened North Fork Table & Inn in Southold. Located at 58775 County Rd. 48, Greenport; 631-477-1910; soundviewgreenport.com
Places to Stay on Long Island
If you wanted a bunch of different options to stay on Long Island, be sure to check out these great places to stay in Montauk, this Guide to Shelter Island hotels, 10 Hamptons hotels, 10 North Fork Long Island hotels, and this Guide to Sag Harbor hotels!
Check Out Some Long Island Wine
While you’re on Shelter Island, you’re so close to Long Island Wine Country! It’s another great part of visiting the island. If you’re in the mood for great wine, be sure to check out our Complete List of Long Island Wineries and Long Island Vineyards.
Check out the absolute best Long Island Wine Tours!
If you can’t make it to a tour, why not do some wine tasting at home with Bedell Cellars!
I know you’re getting hungry, so be sure to also check out the best wineries on Long Island for some great food!
While you’re in the area, be sure to check out these 9 relaxing things to do in the North Fork!
When you’re done with all of this wine drinking and relaxing, how about making it a weekend? Here are 10 great North Fork Long Island hotels to enjoy as well.
More From The Long Island Local
Maybe grab a freshly brewed beer at these Long Island breweries and when you’ve had your fill of vino!
The bounty of great food on Long Island seems endless! From great steakhouses on Long Island to great Greenport restaurants to Long Island lobster rolls, there’s so much to enjoy. And how about all the wonderful restaurants on the water Long Island?! Or maybe check out some Long Island oyster farms!