Southold Holidays

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Things to do near Southold

Southold offers a delightful blend of outdoor activities and romantic settings, perfect for an unforgettable getaway. Visitors can indulge in skiing at local resorts or explore captivating art exhibits that showcase the area's creative spirit. Whether you're looking for adventure or a serene escape, Southold's charming atmosphere and diverse attractions promise an enjoyable experience.

Shopping

The Greenport Farmers' Market, located 6.4km from Southold, offers a vibrant public market experience with local produce and crafts. The Style Bar and Love Lane, both 12.9km away, provide charming shopping areas with a family-friendly atmosphere and a variety of unique gifts. If you're up for a drive, consider exploring further options.

Recreation

At Goldsmith's Inlet Park, enjoy serene walks along scenic trails while embracing the tranquil atmosphere. Noyac Golf Club offers invigorating rounds of golf amid lush landscapes, perfect for sports enthusiasts. For family fun, the Shelter Island Whale's Tail mini-golf provides a delightful blend of adventure and leisure.

Adventure

Experience the thrill of freefall at Long Island Skydiving Center, located 38.6km from Southold, where the excitement of air sports awaits. Alternatively, splash around at Splish Splash Water Park, located 30.6km away, for family fun and adventure, or enjoy the adrenaline at Riverhead Raceway, located 29.0km from Southold.

Nightlife

In Southold, the Greenport Carousel offers a whimsical outdoor experience, just 6.4km away, while the Bay Street Theatre, located 12.9km away, enchants with its romantic and cultural performances. For a family-friendly cinematic experience, the Regal UA Hampton Bays, 16.4km away, provides delightful films for all ages.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Southold

Southold is an idyllic destination for outdoor enthusiasts and couples seeking a romantic getaway, offering a delightful blend of entertainment and cultural experiences. Visitors can explore beautiful beaches, serene urban parks, and intriguing history museums, ensuring a well-rounded holiday that caters to those who appreciate nature and history alike. Discover the charm of Southold while indulging in its outdoor activities and cultural attractions.

  • Harbes Family Farm: Experience the charm of rural life at Harbes Family Farm, where you can enjoy seasonal activities like fruit picking, hayrides, and exploring the picturesque fields. Perfect for families, it offers a delightful insight into farm life just 16.1km from Southold.
  • The Hamptons Beaches: Immerse yourself in the relaxed beach vibes at The Hamptons Beaches, located 19.3km away. With stunning sandy shores and inviting waters, it's an ideal spot for sunbathing, swimming, or enjoying a leisurely stroll along the coastline.
  • Railroad Museum of Long Island: Discover the rich history of rail transportation at the Railroad Museum of Long Island, just 6.4km from Southold. This cultural gem showcases fascinating exhibits and vintage trains, offering a unique glimpse into the region's railway heritage.

Best time to go to Southold

The best time to visit Southold can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Southold falls in August, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Southold falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighSlightly High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

Booking tips and Expedia advantages for Southold

To save money during your visit to Southold, plan your trip between January and March when accommodation prices are lower, especially on Tuesdays. Avoid weekends, particularly Saturdays, for the best rates. Use Expedia’s search tool to filter hotels by budget and location, and consider booking a package deal that combines flights, hotel, and activities for extra savings. Additionally, explore free local activities to enhance your experience without breaking the bank. Being strategic about your travel dates and utilising online tools can significantly reduce your overall expenses.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, including your budget, preferred location, and the type of hotel you desire. For the best prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy savings by combining your Southold hotel reservations with your flights and activities through an Expedia package.

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 Rp3.085.812 per night from 16 Nov to 17 Nov
Rp3.085.812
Rp3.941.441 total
16 Nov - 17 Nov
includes taxes & fees
9.4/10 Exceptional! (218 reviews)
Everything was Amazing!

Reviewed on 28 Oct 2025

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 Rp1.332.143 per night from 4 Nov to 5 Nov
Rp1.332.143
Rp1.531.964 total
4 Nov - 5 Nov
includes taxes & fees
7.8/10 Good! (1,007 reviews)
Clean room excellent staff extremely helpful plenty of parking

Reviewed on 25 Oct 2025

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is Rp1.484.317 per night from 1 Dec to 2 Dec
Rp1.484.317
Rp1.706.965 total
1 Dec - 2 Dec
includes taxes & fees
7.6/10 Good! (1,008 reviews)
It was a nice clean hotel.

Reviewed on 27 Oct 2025

Quality Inn Old Saybrook - Westbrook
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.

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What to do in Southold

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