Find 5 Star Hotels in Southold, NY

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Check availability on Southold 5 Star Hotels

Tonight
6 Jun - 7 Jun
Tomorrow
7 Jun - 8 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

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

Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (69)
"I loved The Mill House Inn! Kenny, the general manager was so amazing! He was so kind and accommodating, and went above and beyond to make my stay wonderful! He is a gem! I got a free upgrade as it was a slow weekend in early spring. My room was large and amazing and so comfortable. Can’t wait to stay here again on my next visit! Thank you Kenny!🙏"
The price is AED 2,204
AED 2,770 total
includes taxes & fees
8 Jun - 9 Jun
Mill House Inn
Casa Newmark Holiday home 7 BestStayz.1
House | Outdoor pool

Casa Newmark Holiday home 7 BestStayz.1

5.0 star property
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.
Baron's Cove

Baron's Cove

31 West Water Street, Sag Harbor, NY
Get rates
9/10 Wonderful! (247 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

Come to Southold and enjoy its wineries, island views, and beaches.

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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

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.