Compare and book 5 Star hotels in Southold, New York

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Check availability on Southold 5 Star Hotels

Tonight
23 Apr - 24 Apr
Tomorrow
24 Apr - 25 Apr
This weekend
24 Apr - 26 Apr
Next weekend
1 May - 3 May

Our top choices for Southold 5-star hotels

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, (83 reviews)
"It is a very nice place, the staff is very friendly and the breakfast is very good. Also they have delicious teas, coffee, hot cider and snacks. We definitely recommend this hotel "
United States
Eliane
The price is 9.873.000 ₫
12.408.123 ₫ total
includes taxes & fees
30 Apr - 1 May
Mill House Inn
House | Outdoor spa tub

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.
Sound View Greenport

Sound View Greenport

58775 County Rd 48 Greenport NY
The price is 5.426.407 ₫ per night from 26 Apr to 27 Apr
5.426.407 ₫
6.951.646 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8.4/10 Very Good! (639 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
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Southold?
There are various pricing options for a 5-star hotel in Southold on Expedia. How much you'll pay will depend on your travel dates, trip length and other factors. Compare all of the available properties for your chosen dates and use our pricing and other filters to score the ideal upscale stay.

  • Search for the lowest price per night from 6.951.646 ₫

What makes a hotel 5 stars in Southold?
Exceptional guest service is the foundation of every 5-star hotel in Southold. From the moment you arrive, staff attend to your every need, whether arranging valet parking or providing in-room beauty treatments. Additionally, hotels have to feature top-rate amenities to be entitled to a 5-star rating. These can include luxury bathrobes, saunas or spas, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Southold?
Find a luxury escape that includes your lodging, food, activities and entertainment in Southold with the help of our filters. Search for hotels with a 5-star rating and click on the "All inclusive" filter. Double-check what's included in the purchase price. That way, you'll be ready to maximise the many perks on offer as soon as you arrive.