Book the Best HISTORIC Hotels in Southold in 2026

Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Southold Historic Hotels

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Southold historic hotels

American Beech in Greenport - Deluxe King Suite 12

Greenport

CA $323 total

includes taxes & fees

Mar 12 - Mar 13

American Beech in Greenport NY - King Suite 1

Greenport

Dean J.

CA $379 total

includes taxes & fees

Mar 15 - Mar 16

American Beech - Deluxe King Suite 14

Greenport

Suzanne B.

CA $379 total

includes taxes & fees

Mar 12 - Mar 13

American Beech in Greenport - Petite King Room 7

Greenport

Parent From The Heart, Inc. E.

CA $272 total

includes taxes & fees

Mar 12 - Mar 13

American Beech - Deluxe King 5

Greenport

Ayana M.

CA $414 total

includes taxes & fees

Mar 15 - Mar 16

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton

Harry V.

CA $1,272 total

includes taxes & fees

Mar 13 - Mar 14

American Beech in Greenport - Deluxe King Suite 11

Greenport

CA $414 total

includes taxes & fees

Mar 15 - Mar 16

American Beech - King Suite 2

Greenport

Patrick M.

CA $379 total

includes taxes & fees

Mar 15 - Mar 16

View all properties

Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

6/10 Okay

"Very welcoming staff. Average accommodations but comfortable and convenient to supermarket. "

Spark by Hilton Guilford

10/10 Excellent

"I was pleasantly surprised with every aspect of my stay Sparks by Hilton, especially the price. My only complaints, which isn’t much in the grand scheme of things, is they don’t provide cups (plastic or otherwise) in the room and for a newly refurbished property, the toilet was small, low to the ground and seemed older. I will definitely be staying there again. The location is ideal for the area. "

Frequently asked questions

What should a history buff expect from a stay in Southold?

You're likely already making plans to see the historical sites during your trip to Southold. Also explore all there is to see and do such as the wineries and beaches

How many historical hotels are there in Southold?

In Southold, there are 148 hotels and other lodging options bookable on Expedia, including 2 historic hotels or hotels close to historic sites.

What are the must-see historical sites and other places to visit in Southold?

Southold is notable for landmarks like Horton Point Park. The picturesque setting of Horton Lane Beach and McCabe's Beach exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Croteaux Vineyards and Osprey's Dominion.

What is a historic hotel like in Southold?

By booking a historic hotel, guests can enjoy a vacation someplace that has a national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often found in the guestrooms or communal spaces of such hotels in Southold, giving a historical feel.

What is the difference between a historic hotel and a heritage hotel?

"Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The building and architecture of historic hotels tend to be the most significant aspect. For a heritage hotel, it's mainly the cultural value and how it inspired the community.

Do historic hotels in Southold have modern facilities?

Hotels include modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in any hotel should be available at a historic hotel. When you choose a historic hotel in Southold, don't worry that you'll find yourself staying at a place that is rundown or uncomfortable.

Explore a world of travel with Expedia

Flights from Toronto (YYZ) to New York (NYC)

Book Historic Hotels in Southold on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Southold Historic Hotels

Our top choices for Southold historic hotels

American Beech in Greenport - Deluxe King Suite 12