Southold Holidays

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Top hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is Rp6.650.580 per night from 3 Aug to 4 Aug
Rp6.650.580
Rp8.045.487 total
3 Aug - 4 Aug
includes taxes & fees
9.4/10 Exceptional! (299 reviews)
"Si"

Reviewed on 22 Jul 2026

The Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is Rp1.658.933 per night from 23 Jul to 24 Jul
Rp1.658.933
Rp1.907.755 total
23 Jul - 24 Jul
includes taxes & fees
8/10 Very good! (1,002 reviews)
"yes"

Reviewed on 22 Jul 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is Rp6.611.405 per night from 6 Aug to 7 Aug
Rp6.611.405
Rp9.086.353 total
6 Aug - 7 Aug
includes taxes & fees
Sound View Greenport
See all 4,375 properties in Southold
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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.
See properties

What to do in Southold

great fun with friends

Full Day Private Long Island Wine Tours from New York City

Rp3.375.351
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold

Frequently asked questions

How much does a Southold holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday to Southold costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Southold?
January, February and March are great times to look for cheap Southold holiday packages. Choosing to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Southold?
Dedicate at least 3 days for your Southold holiday to immerse yourself in everything that makes this place unique. Explore popular areas, including Greenport West and Pipes Cove. Then head to the major sights like Osprey's Dominion and Croteaux Vineyards. With a good itinerary, you can keep busy with room for some me-time too. Want to travel beyond Southold? Consider an excursion or two.
How to find the best Southold package deals?
Bagging a cheap Southold package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Southold package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Southold holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalise your Southold escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Southold?
If you're planning a spur-of-the-moment Southold holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Southold?

  1. Choose your dates: The things you'd like to do in Southold and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the largest expense during your trip to Southold.
  3. Decide how long to go for: Now that you know more about Southold, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customised Southold holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.