Title: Visit Southold: 2026 Travel Guide for Southold, New York | Expedia.com

[Hotels in Southold](https://expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)[Vacation Rentals in Southold](https://expedia.com/Southold-Vacation-Rentals.d183719.Travel-Guide-VacationRentals)[Flights to Southold](https://expedia.com/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Things to do in Southold](https://expedia.com/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)[Car Rentals in Southold](https://expedia.com/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.com/Southold.d183719.Destination-Travel-Guides)

# Southold, NY

## Travel Guide

![Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Tranquil sunset seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/2f5d59dd-9baa-4fe4-96b8-839361de94bb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Tranquil seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/31ba309a-453e-45eb-ba2b-eccf35423a5b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![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. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Southold

Things to do

Reviews

- Southold Hotel Deals
- Vacation Rentals in Southold

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/968755d8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Shoals Suites and Slips

61600 Main Rd Southold NY

$159 nightly

$182 total

Feb 19 - Feb 20

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! (239 reviews)

Room was great. Clean and comfortable. Glad I found this place and will be back.

Reviewed on Jan 22, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=76716269&PinnedHotelID=76716269&HadPinnedHotel=true&regionId=183719)

![Vine & Sand](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718085/a9ca389a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Vine & Sand

47100 New York 25 Southold NY

$327 nightly

$374 total

Feb 22 - Feb 23

Total with taxes and fees

Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Croteaux Vineyards and Corey Creek ...

9.6/10 Exceptional! (15 reviews)

Vine + Sand was wonderful. The hosts were so friendly and it was close to many wineries.

Reviewed on Jan 19, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=96718085&PinnedHotelID=96718085&HadPinnedHotel=true&regionId=183719)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sound View Greenport

58775 County Rd 48 Greenport NY

$155 nightly

$178 total

Feb 24 - Feb 25

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! (609 reviews)

This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=15273178&PinnedHotelID=15273178&HadPinnedHotel=true&regionId=183719)

[See all 4,323 properties in Southold](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&regionId=183719)

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.

![The SandPiper ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698318/9eada5e0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The SandPiper 

 Greenport, NY

Stay at this vacation home in Greenport. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...

9.6/10 Exceptional! (32 reviews)

The host was very understanding about some last minute events that affected our trip

Reviewed on Jan 26, 2026

[](https://expedia.com/Greenport-Hotels-The-SandPiper.h89698318.Hotel-Information)

![Aqua Vista ](https://images.trvl-media.com/lodging/90000000/89700000/89698400/89698360/91dd1778_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Aqua Vista 

 Greenport, NY

Stay at this vacation home in Greenport. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Railroad Museum of Long Island and East End ...

9.8/10 Exceptional! (24 reviews)

This place was a dream. Super comfortable. The host has thought of everything, including a sweet holiday welcome gift. Everything is in walking distance- I didn't use my car for 2 days. It was wonderful to walk along the water into town. What a great retreat!

Reviewed on Jan 2, 2026

[](https://expedia.com/Greenport-Hotels-Aqua-Vista.h89698360.Hotel-Information)

![Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!](https://images.trvl-media.com/lodging/34000000/33570000/33561600/33561503/ca104a55_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

 Hampton Bays NY

Book a stay at this beach vacation home in Hampton Bays. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Meschutt Beach and Good ...

9.4/10 Exceptional! (131 reviews)

We absolutely loved the place and had a great time. There was plenty of space for the kids to spread out and enjoyed the indoor fireplace. The sunrise views were amazing and it's always special to stay on the water. Communication with the owner was great. We hope to visit again.

Reviewed on Jan 11, 2026

[](https://expedia.com/Hampton-Bays-Hotels-Beautiful-Waterfront.h33561503.Hotel-Information)

[See all properties in Southold](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=183719&sort=VACATION_RENTAL)

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.

## Check Southold hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2026-02-08&endDate=2026-02-09)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2026-02-09&endDate=2026-02-10)[Feb 9 - Feb 10](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2026-02-09&endDate=2026-02-10)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=183719&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)

### Popular places to visit

![Cleanest, prettiest winery on the east end of Long Island!  Try the Cuvee' Rose!](https://images.trvl-media.com/place/183719/1c666367-92bc-4b18-b16d-e60341a06481.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sparkling Pointe

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. 

[](https://expedia.com/Sparkling-Pointe-Southold.d6327589.Vacation-Attraction)

#### Horton Lane Beach

Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets. 

[](https://expedia.com/Horton-Lane-Beach-Southold.d553248635983992604.Vacation-Attraction)

#### Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area. 

[](https://expedia.com/Sanninos-Bella-Vita-Vineyard-Southold.d6327435.Vacation-Attraction)

#### Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area. 

[](https://expedia.com/Croteaux-Vineyards-Southold.d6326852.Vacation-Attraction)

#### The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area. 

[](https://expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction)

#### Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area. 

[](https://expedia.com/Ospreys-Dominion-Southold.d6326243.Vacation-Attraction)

### Things to do

![Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day](https://mediaim.expedia.com/localexpert/49191765/ac89ae9d-97f9-4af1-a397-a2a9a43ec484.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Long Island Wine Tour North Fork Sights, Bites & Flights Full-Day

$559

per adult

[](https://expedia.com/things-to-do/long-island-wine-tour-north-fork-sights.a49191765.activity-details)

[See all activities in Southold](https://expedia.com/Things-To-Do-In-Southold.d183719.Travel-Guide-Activities)

## Reviews of Southold

4.4

Top Destination

5 - Excellent

13

4 - Good

5

3 - Okay

2

2 - Disappointing

0

1 - Terrible

1

### 5/5 - Excellent

Verified traveler

Head into Greenport for the brewery, Aldo’s for coffee, Crazy Beans, and the waterfront. Pindar vineyard was a great time and there is a nice family farm directly across the street.

### 3/5 - Okay

Verified traveler

Expensive

### 5/5 - Excellent

Verified traveler

I love Southold and all the areas on the Northfork side.

### 5/5 - Excellent

Verified traveler

Quiet, North Fork town.

### 3/5 - Okay

Louise

Lots of wineries to visit with excellent wines. Tastings can be a bit expensive. One vineyard charged $16 for 3 - 2 oz tastings. It would have been less expensive to just buy a glass or a bottle of wine. A glass of wine was $11 - $13.

### 4/5 - Good

Trish

Took a wonderful Jet Ski tour around Shelter Island (Peconic Water Sports), Spent a wonderful day in Greenport.

## Cities near Southold

![The one of best destinations for summer vacation!#Trove#Summer](https://images.trvl-media.com/place/110728/bf7f0ae9-ecfe-4ab0-b34c-f44de31622e4.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Greenport

![Sunset along the beach at Towd Point in Southampton, Long Island, New York.](https://images.trvl-media.com/place/144477/d8201a6e-8861-410b-8d02-9fda68bbf3f3.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Peconic

![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Shelter Island

![coastal landscape at Greenport at the islands of shelter islands heights, county New York](https://images.trvl-media.com/place/183716/7e82dc91-d6c1-40f0-b4ce-69678c9bd599.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Shelter Island Heights

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- [Hotels near Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Hotels.0-l6327144-0.Travel-Guide-Filter-Hotels)
- [Hotels near Greenport Station ](https://www.expedia.com/Greenport-Station-Hotels.d6186190.Travel-Guide-Hotels)
- [Hotels near East End Seaport Maritime Museum ](https://www.expedia.com/East-End-Seaport-Maritime-Museum-Hotels.0-l6326863-0.Travel-Guide-Filter-Hotels)
- [Hotels near 8 Hands Farm ](https://www.expedia.com/8-Hands-Farm-Hotels.0-l553248635974530505-0.Travel-Guide-Filter-Hotels)

- [Flights from Town of Southold Town ](https://www.expedia.com/lp/flights/553248635976002319/flights-from-town-of-southold-town)
- [Flights to Peconic ](https://www.expedia.com/Cheap-Flights-To-Peconic.d144477.Travel-Guide-Flights)
- [Flights from Peconic ](https://www.expedia.com/lp/flights/144477/flights-from-peconic)
- [Flights to Shelter Island Heights ](https://www.expedia.com/Cheap-Flights-To-Shelter-Island-Heights.d183716.Travel-Guide-Flights)
- [Flights from Shelter Island Heights ](https://www.expedia.com/lp/flights/183716/flights-from-shelter-island-heights)

- [Sparkling Pointe ](https://www.expedia.com/Sparkling-Pointe-Southold.d6327589.Vacation-Attraction)
- [The Old Field Vineyards ](https://www.expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction)
- [Mattebella Vineyards ](https://www.expedia.com/Mattebella-Vineyards-Southold.d6326068.Vacation-Attraction)
- [Corey Creek Winery ](https://www.expedia.com/Corey-Creek-Winery-Southold.d6326844.Vacation-Attraction)
- [Horton Point Park ](https://www.expedia.com/Horton-Point-Park-Southold.d6064489.Vacation-Attraction)
- [Visit Peconic ](https://www.expedia.com/Peconic.dx144477)
- [Sannino's Bella Vita Vineyard ](https://www.expedia.com/Sanninos-Bella-Vita-Vineyard-Southold.d6327435.Vacation-Attraction)
- [Peconic Vacations ](https://www.expedia.com/Peconic.d144477.Destination-Travel-Guides)
- [Goldsmith's Inlet Park ](https://www.expedia.com/Goldsmiths-Inlet-Park-Peconic.d6326890.Vacation-Attraction)
- [Raphael Winery ](https://www.expedia.com/Raphael-Winery-Peconic.d6327146.Vacation-Attraction)
- [Crescent Beach ](https://www.expedia.com/Crescent-Beach-Shelter-Island-Heights.d553248621554204758.Vacation-Attraction)
- [Lenz Winery ](https://www.expedia.com/Lenz-Winery-Peconic.d6326930.Vacation-Attraction)
- [Pindar Vineyards ](https://www.expedia.com/Pindar-Vineyards-Peconic.d6326965.Vacation-Attraction)
- [Sunset Beach ](https://www.expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction)
- [Bedell Cellars ](https://www.expedia.com/Bedell-Cellars-Cutchogue.d553248621532665643.Vacation-Attraction)
- [Visit Shelter Island Heights ](https://www.expedia.com/Shelter-Island-Heights.dx183716)
- [Visit Greenport ](https://www.expedia.com/Greenport.dx110728)
- [Railroad Museum of Long Island ](https://www.expedia.com/Railroad-Museum-Of-Long-Island-Pipes-Cove.d6327144.Vacation-Attraction)
- [Visit Shelter Island ](https://www.expedia.com/Shelter-Island.dx157359)
- [8 Hands Farm ](https://www.expedia.com/8-Hands-Farm-Cutchogue.d553248635974530505.Vacation-Attraction)

- [Car rentals near Peconic ](https://www.expedia.com/Car-Rentals-In-Peconic.d144477.Car-Rental-Guide)
- [Car rentals near Greenport West ](https://www.expedia.com/Car-Rentals-In-Greenport-West.d553248635975876381.Car-Rental-Guide)
- [Car rentals near Pindar Vineyards ](https://www.expedia.com/Car-Rentals-In-Pindar-Vineyards.d6326965.Car-Rental-Guide)
- [Car rentals near Shelter Island Heights ](https://www.expedia.com/Car-Rentals-In-Shelter-Island-Heights.d183716.Car-Rental-Guide)

- [Peconic Vacation Rentals ](https://www.expedia.com/Peconic-Vacation-Rentals.d144477.Travel-Guide-VacationRentals)
- [Shelter Island Heights Vacation Rentals ](https://www.expedia.com/Shelter-Island-Heights-Vacation-Rentals.d183716.Travel-Guide-VacationRentals)

- [Things to do in Peconic ](https://www.expedia.com/Things-To-Do-In-Peconic.d144477.Travel-Guide-Activities)

- Cities near Southold
- Places of interest

[Greenport](https://expedia.com/Greenport.dx110728)[Peconic](https://expedia.com/Peconic.dx144477)[Shelter Island](https://expedia.com/Shelter-Island.dx157359)[Shelter Island Heights](https://expedia.com/Shelter-Island-Heights.dx183716)[Noyack](https://expedia.com/Noyack.dx6217344)

- [Sannino's Bella Vita Vineyard ](https://expedia.com/Sanninos-Bella-Vita-Vineyard-Southold.d6327435.Vacation-Attraction)
- [The Old Field Vineyards ](https://expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction)
- [Sparkling Pointe ](https://expedia.com/Sparkling-Pointe-Southold.d6327589.Vacation-Attraction)
- [Osprey's Dominion ](https://expedia.com/Ospreys-Dominion-Southold.d6326243.Vacation-Attraction)
- [Corey Creek Winery ](https://expedia.com/Corey-Creek-Winery-Southold.d6326844.Vacation-Attraction)
- [Horton Point Park ](https://expedia.com/Horton-Point-Park-Southold.d6064489.Vacation-Attraction)
- [Mattebella Vineyards ](https://expedia.com/Mattebella-Vineyards-Southold.d6326068.Vacation-Attraction)
- [Cooper's Beach ](https://expedia.com/Coopers-Beach-Southampton.d6326842.Vacation-Attraction)
- [Hammonasset Beach State Park ](https://expedia.com/Hammonasset-Beach-State-Park-Madison.d553248621557934267.Vacation-Attraction)
- [East Hampton Main Beach ](https://expedia.com/East-Hampton-Main-Beach-East-Hampton.d6326946.Vacation-Attraction)
- [Splish Splash Water Park ](https://expedia.com/Splish-Splash-Water-Park-Calverton.d6173416.Vacation-Attraction)
- [Wolffer Estates Vineyard ](https://expedia.com/Wolffer-Estates-Vineyard-Sagaponack.d6064497.Vacation-Attraction)
- [Shinnecock Hills Golf Course ](https://expedia.com/Shinnecock-Hills-Golf-Course-Southampton.d6327546.Vacation-Attraction)
- [Hither Hills State Park ](https://expedia.com/Hither-Hills-State-Park-Montauk.d553248621532665771.Vacation-Attraction)
- [Essex Steam Train ](https://expedia.com/Essex-Steam-Train-Essex.d6171206.Vacation-Attraction)
- [Connecticut River ](https://expedia.com/Connecticut-River-United-States-of-America.d553248621555565605.Vacation-Attraction)
- [Orient Point County Park ](https://expedia.com/Orient-Point-County-Park-Orient.d553248621532665781.Vacation-Attraction)
- [Tanger Outlet Center ](https://expedia.com/Tanger-Outlet-Center-Riverhead.d6224628.Vacation-Attraction)
- [Parrish Art Museum ](https://expedia.com/Parrish-Art-Museum-Water-Mill.d6326954.Vacation-Attraction)
- [Raphael Winery ](https://expedia.com/Raphael-Winery-Peconic.d6327146.Vacation-Attraction)
- [Rocky Neck State Park ](https://expedia.com/Rocky-Neck-State-Park-Niantic.d6328112.Vacation-Attraction)
- [Jamesport Vineyards ](https://expedia.com/Jamesport-Vineyards-Riverhead.d553248621532665578.Vacation-Attraction)
- [Sunset Beach ](https://expedia.com/Sunset-Beach-Shelter-Island-Heights.d553248626388141313.Vacation-Attraction)
- [Sag Harbor Marine Park ](https://expedia.com/Sag-Harbor-Marine-Park-Sag-Harbor.d6327316.Vacation-Attraction)
- [Macari Vineyards ](https://expedia.com/Macari-Vineyards-Mattituck.d6326944.Vacation-Attraction)
- [Hole-in-the-Wall Beach ](https://expedia.com/Hole-In-The-Wall-Beach-Niantic.d553248621532665800.Vacation-Attraction)
- [67 Steps Beach ](https://expedia.com/67-Steps-Beach-Greenport.d553248626388140598.Vacation-Attraction)

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