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Find 5 Star Hotels in Southold, NY from AED 997

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Check availability on Southold 5 Star Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Compare Southold 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Front of property - evening/night
Mill House Inn

Mill House Inn

5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
The price is AED 1,102
AED 1,385 total
includes taxes & fees
9 Dec - 10 Dec
Mill House Inn
House | Outdoor pool
Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1

5.0 star property
Sagaponack
Casa Newmark Holiday home 7 BestStayz.1
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southold.
Madison Beach Hotel

Madison Beach Hotel

94 West Wharf Road Madison CT
The price is AED 879 per night from Jan 1 to Jan 2
AED 879
AED 1,011 total
1 Jan - 2 January 2026
includes taxes & fees
9.4/10 Exceptional! (339 reviews)
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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.

Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold
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.
Photo by Benny Goh
Open Photo by Benny Goh

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Southold?
How much you pay for a 5-star hotel in Southold depends on things such as when you plan to go and the length of your trip. An insider tip for scoring the best deal? Use our pricing filters to check out all of the available hotels for your chosen dates.

  • Search for the lowest price per night from AED 997

What makes a hotel 5 stars in Southold?
From fine dining restaurants and all-day gyms to swimming pools and luxury bedding, the 5-star experience in Southold is all about luxury and relaxation. But it calls for more than just top-notch conveniences to receive a 5-star rating. Accommodations must also provide extraordinary guest-focused services like in-room massage treatments, on-site dry cleaning and laundry and a nightly turn-down service.
Are there any 5-star all-inclusive resorts in Southold?
Use Expedia's filters to find a luxury getaway in Southold where most of what you need is included in the price. From there, narrow down your results for hotels that have a 5-star rating and are deemed "All inclusive." The main thing to look forward to at these stays? Relaxation and indulgence.

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