Find Historic Hotels in Southold, NY

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Check availability on Southold Historic Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Southold Historic Hotels

The Reform Club
Deluxe Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Reform Club

2.0 star property
10.0 out of 10, Exceptional, (2)
"Unique property; lots of attention from staff; close to town."
The Reform Club
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
9.0 out of 10, Wonderful, (103)
"What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!"
The price is AED 1,405
AED 1,642 total
includes taxes & fees
2 Nov - 3 Nov
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (142)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
The price is AED 1,134
AED 1,295 total
includes taxes & fees
5 Nov - 6 Nov
Harpoon House
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (44)
"Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. "
The price is AED 7,613
AED 13,167 total
includes taxes & fees
7 Oct - 8 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Fridge, microwave, oven, stovetop

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (38)
"Great property, would stay here again."
The price is AED 903
AED 1,882 total
includes taxes & fees
8 Oct - 9 Oct
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
American Beech in Greenport NY - King Suite 1
1 bedroom, iron/ironing board, internet

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is AED 768
AED 1,171 total
includes taxes & fees
8 Oct - 9 Oct
American Beech in Greenport NY - King Suite 1
American Beech - King Suite 2
Property grounds

American Beech - King Suite 2

10.0 out of 10, Exceptional, (2)
"Excellent one night stay."
The price is AED 768
AED 1,171 total
includes taxes & fees
7 Oct - 8 Oct
American Beech - King Suite 2
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is AED 731
AED 1,125 total
includes taxes & fees
7 Oct - 8 Oct
American Beech in Greenport - Petite King Room 7
American Beech - Deluxe King 5
Property grounds

American Beech - Deluxe King 5

8.6 out of 10, Excellent, (4)
"I thoroughly enjoyed my stay. I was upgraded before arriving at the hotel and was very pleased with my stay. The staff were kind and accommodating, I will definitely return."
The price is AED 841
AED 1,267 total
includes taxes & fees
7 Oct - 8 Oct
American Beech - Deluxe King 5
American Beech in Greenport - Deluxe King 4
Property grounds

American Beech in Greenport - Deluxe King 4

The price is AED 1,062
AED 1,557 total
includes taxes & fees
3 Nov - 4 Nov
American Beech in Greenport - Deluxe King 4
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.
View all properties

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Fantastic stay. Will return."
Ian 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

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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 153 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 McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Sparkling Pointe and Croteaux Vineyards.
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.