Photo by Benny Goh

Southold 5 Stars Hotels

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Check availability on Southold 5 Star Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Southold 5-star hotels

Front of property - evening/night
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is NT$14,931
NT$18,765 total
includes taxes & fees
Dec 31 - 2026/1/1
Mill House Inn
House | Outdoor pool
Casa Newmark Holiday home 7 BestStayz.1

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 NT$8,647 per night from Jan 1 to Jan 2
NT$8,647
NT$9,944 total
Jan 1 - 2026/1/2
includes taxes & fees
9.4/10 Exceptional! (341 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

Top Southold Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Southold?
The amount you pay for a 5-star hotel in Southold can vary based on when you decide to travel and how long you plan to be away, among a range of factors. Take advantage of our price per night filter and other search tools to score the best deal on a high-end stay.

  • Search for the lowest price per night from NT$6,504

What makes a hotel 5 stars in Southold?
Flawless guest service is the hallmark of every 5-star hotel in Southold. From the minute you arrive, staff ensure your every need is met, whether recommending activities or providing in-room massages. Plus, hotels have to offer superior amenities to meet the standard for a 5-star rating. These can include luxury baths, saunas or spas, swimming pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Southold?
Find an indulgent retreat that includes your lodging, food, activities and entertainment in Southold with our handy filter tool. Search for hotels rated 5 stars and click on the "All inclusive" filter. Double-check what's included in the upfront price. That way, you can take full advantage of all the premium perks from the moment you step into the lobby.

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