Are there any 5-star vacation rentals in Southold?

Our site doesn't offer any 5-star vacation rentals in Southold. However, you can still find a range of top-rated escapes where the only thing on your itinerary will be to kick back and enjoy yourself. See what's available by checking out our vacation rentals 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.

Find 5 Star Hotels in Southold, NY from $200

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

Mill House Inn

Pantigo Road Historic District

"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...

margaret

$330 nightly

Dec 10 - Dec 11

Total with taxes and fees

Casa Newmark Holiday home 7 BestStayz.1

Sagaponack

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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

94 West Wharf Road Madison CT

$242 nightly

$278 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

9.4/10 Exceptional! (339 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

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Top Southold Hotel Reviews

Find out more about Southold

There's nothing wrong with enjoying the finer things in life. Why not ask for complete opulence on your holiday to Southold? There's no reason to delay a getaway to Southold any longer. You'll join the multitudes of vacationers who have made Southold so fashionable recently. Additionally, the hotels in this area are known for guest services, so you know you'll be looked after during your getaway. Don't wait any longer. Book one of Expedia's luxurious 5-star hotels in Southold and get ready to enjoy the getaway of a lifetime.

Get a Great Deal on 5-Star Hotels in Southold

Don't be afraid to live the high life while you're on vacation, along with the best conditions. High-end restaurants, concierges, and in-room massages are all at the ready. You're sure to find exactly the accommodation you need. Additionally, the hotels in this area receive high marks for customer satisfaction, so you know you'll want for nothing during your getaway. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A mud wrap treatment that will leave you feeling great? Butler services? No matter what you want on a perfect getaway, you're bound to find it here.

Ready for experiences outside your hotel room? You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Southold are waiting for you to rest up after an exciting day. Ready to learn more? Plenty of visitors recommend this location.

Your Getaway Starts Today

The results are in, and Southold 5-star hotels are the place to be when you book your next vacation. These beautiful hotels are highly rated by the guests who stay in them, and you're about to join their ranks. It's time to indulge yourself -- Expedia can help you land a great deal on accommodation. Choose one of the 5-star hotels in Southold today and relax in total tranquility when you're ready.

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 $200

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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