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Sannino Bed & Breakfast is set among the winery’s vines. (Photo Credit: David Benthal)

Whether you prefer a laid-back, rustic vibe or want to indulge in a refined, romantic weekend, spending a winter’s weekend on the North Fork is one of the best ways to experience the characteristic charm of Long Island’s wine region.

This list highlights 2021 winter specials at a few of our favorite North Fork and Shelter Island bed and breakfasts.

The Bay Breeze Inn, South Jamesport

The rustic-chic Bay Breeze Inn offers a main house with six rooms, named after North Fork hamlets, and a stand-alone cottage with two apartment-styled units each sleeping four guests. Cozy up by the inn’s fire pit with a glass of wine and look out to Peconic Bay. 

The inn’s new restaurant, The Watershed Kitchen and Bar, serves breakfast Wednesday-Sundays. In addition to breakfast, the restaurant offers a daily menu with sandwiches and entrees like Cauliflower Steak and Bolognese. Brunch is served on weekends beginning at 11:30am. 

Bay Breeze Inn is currently offering a mid week Monday-Thursday special; call directly for the rate. Essential workers in service industries also receive 10% off their reservation with no expiration. 

46 Front Street, South Jamesport, (631) 779-3454

The Mattituck is one of the king sized rooms at the Bay Breeze Inn (Credit: Monique Singh-Roy)

The Candlelite Inn, Shelter Island

House in a 181-year-old Victorian, the Candlelite Inn offers a peaceful romantic getaway into the quiet countryside of Shelter Island. Each of the five guest rooms has a private bath, and there is also a separate Honeymoon cottage with a King size sleigh bed and a double whirlpool bath.

The Inn is a short walk away from Vine Street Café and the miles of trails in the Mashomack Nature Preserve. 

Breakfast is continental style, served individually wrapped. With advance notice, guests may also schedule hair services including highlighting, styling and more. 

3 S Ferry Road, Shelter Island,  (631) 749-0676

candlelite inn shelter island
The sitting room at the Candlelite Inn on Shelter Island. (Photo Credit: Tara Smith)

The Coffey House B&B

Open year round, this B&B in East Marion is set on two acres and includes four beautifully appointed guest rooms. These include a luxurious suite with an oversized soaking tub and glass-enclosed shower.  

Enjoy staying in with their variety of board games, books, and a full DVD library, plus refreshments in their recreation room. In the morning, you are greeted to a three-course breakfast with freshly baked goods, and the house specialty frittatas made with fresh eggs from the North Fork Egg Farm.

This winter, the Coffey House is offering guests a $50 gift card to the Hellenic Restaurant for those that reserve two night stays. The restaurant is right next door to the B&B and the offer is valid through April 30. 

5705 Main Road, East Marion, (631) 477-2107

Coffey House Bed and Breakfast (Photo Credit: Cyndi Murray)

Sannino Vineyard Bed and Breakfast in Cutchogue

In the heart of North Fork’s wine country in Cutchogue is Sannino Vineyard Bed and Breakfast

Stay in the exclusive Tuscan Suite or Tuscan Villa, both of which sleep two and have all of the amenities for a romantic getaway. Included in your stay is a full, chef’s choice hot breakfast. Contactless check-in and checkout is also included.

Guests also enjoy a complimentary wine tasting and cheeseboard at the B&B’s sister winery, Sannino Vineyard, located in Cutchogue, as well as a discount card to local wineries, shops and restaurants. Please note that reservations at their tasting house are required on weekends, and recommended on weekdays. Call for B&B rates.

7490 Alvahs Lane, Cutchogue, (631) 734-8282

One of the rooms at Sannino Bed & Breakfast. (Photo Credit: Cyndi Murray)

Shorecrest Bed & Breakfast, Southold

Nestled between the Long Island Sound and Hashamomack Pond in Southold is the five-room Shorecrest Bed and Breakfast. This winter, cozy up with spectacular water views sprinkled with a mix of comfort and Old World charm. Several of the rooms have fireplaces, four-poster beds or jacuzzi tubs.

Recently, the B&B installed a state-of-the-art ultraviolet air cleaning system. Guests are served at separate tables as opposed to the traditional family style seating in the formal dining room. When the weather gets warmer, breakfast may be served on the deck. 

Want to make your stay even more special? Add a Champagne picnic welcome, a wine and cheese surprise or a 90-minute massage. There is a 10% discount on 2 nights midweek. 

54300 County Route 48, Southold, (631) 765-1570

The ‘Rose Room’ at Shorecrest Bed and breakfast. (Photo Credit: Shorecrest B&B)

The Farmhouse Bed & Breakfast, Cutchogue

The Farmhouse B&B, now under new ownership, continues to provide the tranquil simplicity it has been lovingly known for. Suite 1, on the ground floor, features a four-poster bed, fieldstone fireplace with an antique beam mantel, and a private bath with a heated floor and double shower. 

Public areas offer more opportunities to get cozy in winter, with a fireplace in the lounge area and a fire pit out back.

Daily breakfast is included and shows off the best of local farm-to-table cuisine. The B&B serves eggs from their own chickens, honey from its own honeybees, and jam made from their own berry bushes. They also feature nearby purveyors on their menu like Wickham’s for produce, bacon from 8 Hands Farm, coffee from Hampton Coffee Company, and chocolates from North Fork Chocolate Company. 

Farmhouse B&B offers discounts to returning guests and those who book all three rooms.  Look out for specials in the near future.

1855 Depot Lane, Cutchogue, (631) 734-8539

Farmhouse Bed & Breakfast on Depot Lane in Cutchogue. (Photo Credit: Cyndi Murray)

The Stirling House Bed & Breakfast

The Stirling House is a charming waterfront inn in Greenport Village. The village location means you’re just a short walk from many shops and restaurants (as well as the Long Island Railroad Station). Guestrooms, some with king beds, overlook Greenport Harbor and Shelter Island.

Each guestroom has its own dining room for the utmost comfort and privacy. Breakfast may be the highlight of your stay. A full breakfast awaits created by Chef Clayton, who studied at The French Culinary Institute; his specialty is the Stirling House Dutch Pancake. Complimentary wine and homemade snacks are also on hand.  

Open year round, The Stirling House has a two-night minimum.

104 Bay Avenue, Greenport, (631) 477-0654

Stirling House in Greenport. (Photo Credit: Cyndi Murray)