Southold, NY

Travel Guide

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$254 nightly
The price is $286 total per night from Oct 1 to Oct 2
$286 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (340 reviews)
"Lovely property in a beautiful setting. Really enjoyed the large rooms and the location for exploring North Fork."

Reviewed on Sep 18, 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
$80 nightly
The price is $93 total per night from Oct 8 to Oct 9
$93 total
Oct 8 - Oct 9
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,005 reviews)
"Nothing fancy, but clean and nice!"

Reviewed on Sep 19, 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$825 nightly
The price is $943 total per night from Oct 3 to Oct 4
$943 total
Oct 3 - Oct 4
Total with taxes and fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (731 reviews)
"Nice property clean rooms unique having room right on the ocean front was surprised by a pretty nice breakfast many choices food coffee which is always important overall the property is well located to visit surrounding farms and vineyards and short car ride to restaurants and water front"

Reviewed on Sep 19, 2026

Sound View Greenport
See all 4,302 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.
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.6/10 Exceptional! (56 reviews)
"Very new and clean property very helpful and friendly staff ..... some areas where the rvs are the view not great ..... otherwise all good"

Reviewed on Sep 18, 2026

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
Cliffside Resort Condominiums
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (323 reviews)
"Great location by the ocean. Friendly staff, very helpful. Unfortunately not as clean as we wished and the rooms are quite dated."

Reviewed on Sep 8, 2026

Windward Shores Ocean Resort
See all 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)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
See properties

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

$175
per adult
Sunday Brunch Sail in Greenport
great fun with friends

Full Day Private Long Island Wine Tours from New York City

$189
per adult
Full Day Private Long Island Wine Tours from New York City
See all activities in Southold

Frequently asked questions

Is Southold worth visiting?
Southold is worth visiting for its vineyards, including Croteaux Vineyards and Sannino's Bella Vita Vineyard, where travelers can enjoy local wines. The destination also offers delicious North American and seafood dining options. Additionally, Southold provides practical transit access via train, making it convenient for travelers to explore the area.
When is the best time to visit Southold?
The best time to visit Southold is from June through August, which is generally a popular period for travelers. For fewer crowds and better value, the quieter months of November through January are a good option, offering a more relaxed experience with potentially lower rates.
What is Southold known for?
Southold is known for its vineyards, such as Croteaux Vineyards, Sannino's Bella Vita Vineyard, and Mattebella Vineyards. Travelers can explore these local wineries and enjoy the area's North American food culture, making it a destination for culinary and wine experiences.
What is a good itinerary length for Southold?
A good itinerary length for Southold is one to two days to enjoy the local vineyards like Croteaux Vineyards and Sannino's Bella Vita Vineyard, perhaps with a Long Island Wine Tour. An extended stay of three to four days lets travelers explore more vineyards, relax by a lake or beach, and savor North American, seafood, or European cuisine. See Southold Activities.
How do you get around Southold?
Southold travelers can use the train, with service available at Southold Station. For exploring the wider area and getting to various attractions, driving is often the most flexible option. Rideshare services are also available for convenient point-to-point transportation within Southold and nearby areas.
How do I plan a trip to Southold?
To plan your trip to Southold, book flights and hotels early. Explore vineyards like Croteaux Vineyards, perhaps with a Long Island Wine Tour. Consider using the train for local travel. For outdoor activities, have indoor alternatives ready for weather flexibility. Search for places to stay on Expedia.
What cuisines can you find in Southold?
In Southold you can find Mediterranean cuisine, featuring dishes such as hummus, gyros, falafel, and moussaka. Travelers also have options for Italian, Asian, and fresh seafood dishes, alongside classic North American fare.
Can I book a refundable hotel in Southold?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Southold by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Southold with Expedia?
Expedia makes it easier to plan your Southold trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Southold?
The best choice depends on your travel style. Hotels in Southold can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Southold trip on Expedia?
Once you've booked your Southold trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Southold trip?
Expedia offers customer support before, during, and after your Southold trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Southold?
If it's your first trip to Southold, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Southold hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Southold hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Southold

An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport

An aerial view of a coastal landscape with a sandy beach, a bay with small islands, and a dense forested area.

Peconic

A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island

A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights

Explore a world of travel with Expedia