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Find Historic Hotels in Southold, NY

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Check availability on Southold Historic Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Southold Historic Hotels

Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

4.0 star property
East Hampton
9.8 out of 10, Exceptional, (160)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is SAR 996
SAR 1,362 total
includes taxes & fees
9 Dec - 10 Dec
The 1770 House Restaurant & Inn
Garden
The Maidstone

The Maidstone

4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is SAR 976
SAR 1,115 total
includes taxes & fees
2 Jan - 3 January 2026
The Maidstone
1 bedroom, iron/ironing board, internet
American Beech in Greenport NY - King Suite 1

American Beech in Greenport NY - King Suite 1

Greenport
10.0 out of 10, Exceptional, (5)
"Perfect Great place"
United States
Dean J.
The price is SAR 747
SAR 1,149 total
includes taxes & fees
14 Dec - 15 Dec
American Beech in Greenport NY - King Suite 1
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center
9.6 out of 10, Exceptional, (39)
"Great property, would stay here again."
United States
charles b.
The price is SAR 923
SAR 1,911 total
includes taxes & fees
7 Dec - 8 Dec
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Property grounds
American Beech - King Suite 2

American Beech - King Suite 2

Greenport
10.0 out of 10, Exceptional, (2)
"Excellent one night stay."
United Kingdom
Patrick M.
The price is SAR 747
SAR 1,145 total
includes taxes & fees
9 Dec - 10 Dec
American Beech - King Suite 2
Property grounds
American Beech in Greenport - Deluxe King Suite 12

American Beech in Greenport - Deluxe King Suite 12

Greenport
The price is SAR 859
SAR 1,295 total
includes taxes & fees
12 Dec - 13 Dec
American Beech in Greenport - Deluxe King Suite 12
Property grounds
American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3

Greenport
The price is SAR 859
SAR 1,274 total
includes taxes & fees
1 Jan - 2 January 2026
American Beech in Greenport - King Suite 3
Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is SAR 672
SAR 1,038 total
includes taxes & fees
11 Dec - 12 Dec
American Beech in Greenport - Petite King Room 7
Porch
Harpoon House

Harpoon House

3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
Harpoon House
Garden
The Huntting Inn

The Huntting Inn

3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is SAR 1,435
SAR 1,677 total
includes taxes & fees
18 Dec - 19 Dec
The Huntting Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southold Hotel Reviews

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Staff was courteous and the room was spotless. Food service is very good as well. "
Efrem 1-night trip
Posted 4 days ago
Hilton Garden Inn Riverhead

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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 151 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 The Old Field Vineyards and Sparkling Pointe.
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.