Top Southold Hotel Deals

Make the Most of Your Southold Stay

A historic foundation for modern viticulture

Southold stands as New York's oldest English-speaking settlement, established in 1640 by Puritans whose legacy remains visible in the town's federally recognized Historic District. Here, 17th-century Colonial foundations sit alongside Greek Revival and Italianate structures, creating an architectural timeline spanning 3 centuries. This quiet maritime community has evolved from its farming and whaling roots into the North Fork's premier wine destination, where acclaimed estates like Sparkling Pointe produce méthode champenoise wines rivaling French champagne houses. The atmosphere feels deliberately unhurried, offering a refined alternative to the busier Hamptons across Peconic Bay.

Culinary excellence and coastal heritage

North Fork Table & Inn anchors the region's dining scene with farm-to-table cuisine drawing food enthusiasts from Manhattan, while the 1857 Horton Point Lighthouse provides panoramic Long Island Sound views. Nearby Greenport offers walkable waterfront dining and boutique shopping, connected by Long Island Rail Road. The Hampton Jitney's premium bus service features Ambassador-class seating designed for working en route.

Strategic island access

Southold's position makes it ideal for exploring regional island destinations. The North Ferry departs Greenport every 15 minutes for Shelter Island's nature preserves, while Orient Point's Cross Sound Ferry connects to New England in 80 minutes. Properties like The Shoals cater specifically to corporate retreats and executive travelers seeking sophistication and seclusion.

Frequently Asked Questions about Southold

Can I book hotels in Southold on Delta Stays using miles?

Yes, you can book your hotel stay in Southold using your Delta miles, either for the total amount or in combination with money to reserve your stay. Simply log in to your SkyMiles® account, where you will also discover Member-only offers at select properties that could enhance your travel experience.

What are the benefits if I use Delta Stays to book my hotel stay in Southold?

As a SkyMiles Member, you will earn 2 miles per $1 you spend on completed hotel stays and vacation rentals booked through Delta Stays. You will also enjoy access to special Member offers at select properties, and have the flexibility to pay with miles, cash, or a combination of both. To ensure you earn your miles, simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

What is the policy to change or cancel my hotel booking made through Delta Stays?

Each property maintains its own cancellation policy. Make sure to review the cancellation terms displayed in the property information section before confirming your reservation. Some rates may be refundable, while others may be non-refundable. Changes and cancellations to your booking may result in a different amount of miles earned and awarded to your account.

Can my Delta SkyMiles® American Express® Card be used for booking?

Yes, your Delta SkyMiles® Gold, Platinum, or Reserve American Express® Card provides you with additional miles and valuable benefits, including an annual statement credit of up to $200 that you can apply toward prepaid hotels or vacation rentals when booking through Delta Cars and Stays. Note that terms apply to these offerings. To explore all the benefits available with your card, please visit the Delta SkyMiles® American Express Credit Cards page for complete details.

Can I earn MQDs on Delta Stays hotel bookings?

Delta Stays occasionally offers valued promotions allowing SkyMiles Members to accumulate Medallion® Qualification Dollars when booking accommodations through their platform. We invite you to check the Delta Stays MQD Offer page regularly to view current MQD earning opportunities and examine the specific terms and conditions associated with these special offers.

In order to book a hotel on Delta Stays, do I need to be a Delta SkyMiles Member?

No, anyone can book hotels through Delta Stays. However, only SkyMiles Members can earn miles and access Member-only prices and offers. SkyMiles Members earn 2 miles per $1 spent on Delta Cars and Stays purchases (excluding taxes and additional fees). Enrollment in the SkyMiles program comes at no cost. Register today by visiting the delta.com.

On Delta Stays, can I book a vacation rental?

Absolutely, Delta Stays features an extensive collection of vacation rentals in addition to traditional hotel accommodations. You can search for homes, condos, and other unique stays powered by Vrbo on the Vacation Rentals page.

Which hotels have good ratings in Southold?

The Shoals Suites and Slips has a guest rating of 9.4 out of 10, and features a bar/lounge and a cafe.

What's a good time of year to visit Southold?

To experience Southold during great weather, consider a visit in August when the temperature averages 73°F with sunny skies perfect for beaches and wineries. For off-peak prices and more personal attention at tasting rooms, consider visiting during winter months when crowds thin considerably and rates drop.

Which hotels in Southold are near Horton Lane Beach?

This rocky shoreline along Long Island Sound pairs peaceful water views with the historic Horton Point Lighthouse. The adjacent Nautical Museum opens seasonally. Popular hotels include The Farmhouse Bed and Breakfast which is a short drive away. Another top hotel is Silver Sands Motel & Beach Bungalows and it is within a short drive.

Which hotels in Southold are located near Sannino's Bella Vita Vineyard?

This intimate vineyard specializes in sustainable viticulture with expert-guided tastings of their distinctive White Merlot. Book the hands-on "Vine to Wine" experience for winemaking lessons. The Farmhouse Bed and Breakfast is a popular hotel, which is just a short drive away. Another hotel is Silver Sands Motel & Beach Bungalows and it is within a short drive.

Which hotels in Southold are located closest to Croteaux Vineyards?

America's only all-rosé vineyard brings Provence to New York's North Fork with French-inspired wines served in a garden setting. Arrive early on weekends for a table. Popular hotels include The Farmhouse Bed and Breakfast which is a short drive away. Silver Sands Motel & Beach Bungalows is another well-reviewed hotel and it is within a short drive.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar