A calm lake with a forest in the background during sunset.

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Check availability on Southold Historic Hotels

Our top choices for Southold historic hotels

Exterior

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (298 reviews)
"It is a beautiful upscale property. The rooms are very comfortable & had all the amenities you needed. Very good location making it accessible for anything you wanted to do in the area."
United States
Sue
The price is NT$11,998
NT$14,515 total
includes taxes & fees
Aug 3 - Aug 4
The Shoals Suites and Slips
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (667 reviews)
"Location was the best. Enjoyed using the pool. View from the room of the Long Island sound was incredible. We had dinner at Haylard restaurant. On the premises and it was delicious."
United States
rosemary
Sound View Greenport
Exterior

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (355 reviews)
"Great place! We really Enjoyed the room and vibe !"
United States
Zoe
The price is NT$15,744
NT$17,987 total
includes taxes & fees
Jul 23 - Jul 24
Zey Hotel
Property grounds

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1,001 reviews)
"It was in a good location and less expensive than area hotels."
United States
David
The price is NT$3,287
NT$3,781 total
includes taxes & fees
Aug 11 - Aug 12
Pier Blue Inn Old Saybrook - Essex
Outdoor dining

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (40 reviews)
"location!"
United States
Sharon
The price is NT$12,344
NT$14,103 total
includes taxes & fees
Jul 26 - Jul 27
The Chequit
Property grounds

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (325 reviews)
"It was a nice motor lodge with chairs for sitting outside. There’s also a pool out back that was great."
United States
David
The price is NT$3,163
NT$3,637 total
includes taxes & fees
Aug 2 - Aug 3
Clinton Motel
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (94 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is NT$25,773
NT$32,390 total
includes taxes & fees
Aug 9 - Aug 10
The Pridwin Hotel
Exterior

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (245 reviews)
"Staff was helpful. Place is quiet. Room was a little outdated."
United States
Samantha
The price is NT$2,549
NT$2,932 total
includes taxes & fees
Jul 23 - Jul 24
Lamplighter Motel - Clinton, Connecticut
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (34 reviews)
"Great stay & great staff!"
United States
James
The price is NT$17,049
NT$19,479 total
includes taxes & fees
Aug 16 - Aug 17
North Fork Resort
Exterior

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (780 reviews)
"Parking was easy. The grounds and room were clean. It was 5 minutes away from the Jamesport Triathlon."
United States
Diane
The price is NT$5,274
NT$6,025 total
includes taxes & fees
Jul 28 - Jul 29
Shorewood 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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The only thing negative was my wife's fish and chips at dinner. The fish had an ammonia taste but the server graciously removed it from the bill. The Resort and amenities were top notch. I will definitely stay again in the future"
William 1-night trip
Posted 6 hours ago
Saybrook Point Resort & Marina
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"When first arriving, it looks a little aged, but we went into the room. It was clean and the air conditioner worked well. Front desk was helpful with questions. Did not get a chance to use the pool but it looked nice and clean. Though it was a little pricey for a Sunday to Monday stay even for the Hamptons."
Helen 1-night trip
Posted 1 day ago
The Atlantic Hotel

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 141 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. Additionally, you'll find The Hamptons Beaches in the area.
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.

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