Compare and book 5 Star hotels in Southold, New York

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Southold 5 Star Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Southold 5 Star Hotels

Mill House Inn
Front of property – evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is 7.253.400 ₫
9.115.546 ₫ total
includes taxes & fees
27 Oct - 28 Oct
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
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
The price is 6.545.732 ₫ per night from 27 Oct to 28 Oct
6.545.732 ₫
8.769.492 ₫ total
27 Oct - 28 Oct
includes taxes & fees
8.4/10 Very Good! (574 reviews)
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

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

See all hotels in Southold

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 8.769.492 ₫

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia