A calm lake with a forest in the background during sunset.

Find 5 Star Hotels in Southold, NY from $209

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Southold 5 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Southold 5-star hotels

A house with a sloped roof, large windows, and a pathway leading to the entrance.

1. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (90 reviews)
"Proximity to East Hampton stores - so close you can walk to most things, biggest asset of this property. Room was nice, bedding excellent."
United States
Rhett
$411 nightly
The price is $470
Nov 1 - Nov 2
Total with taxes and fees
Mill House Inn
A large house with a swimming pool, hot tub, and outdoor seating area surrounded by trees.

2. 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
$183 nightly
The price is $209 total per night from Nov 23 to Nov 24
$209 total
Nov 23 - Nov 24
Total with taxes and fees
Still don't see what you're looking for?
See all properties in Southold.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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
A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

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 $209

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.

Explore a world of travel with Expedia