Southold hotels

Wed 4/24
Sun 4/28

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Best Southold hotels

Most recommended Southold hotels

Show all
Sound View Greenport - Greenport - Bedroom
Sound View Greenport
8.2 Very good
$502+
$502+
Free Wi-Fi
Pool
Pet friendly
Holiday Inn Long Island - Islip Arpt East - Holtsville - Bedroom
Parking
Free Wi-Fi
Greenporter Hotel
7.9 Good
$293+
$293+
Parking
Free Wi-Fi
Pool
The Chequit
9 Wonderful
$766+
$766+
Parking
Free Wi-Fi
Pet friendly
Shelter Island House
4 Mediocre
$443+
$443+
Parking
Free Wi-Fi
Pool
Pet friendly
American Beech Hotel
8.7 Very good
$572+
$572+
Free Wi-Fi
Pet friendly

Top Southold hotels with parking

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The Pridwin Hotel - Shelter Island Heights - Patio
The Pridwin Hotel
9 Wonderful
$587+
$587+
Parking
Free Wi-Fi

Good to know

Low season

February

High season

September

Average price (weeknight)

$164

Average price (weekend night)

$221
Cheapest month to stay with an average 45% drop in price.
Most expensive month to stay with an average 199% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a hotel in Southold

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Southold hotel deals

  • If you’re looking for a cheap hotel in Southold, you should consider visiting during the low season. You'll find cheaper hotels in Southold in February and January.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Southold if you stay on a Wednesday. The opposite is true for, Friday, which is usually the most expensive day.
  • The cheapest 3-star hotel room in Southold found on KAYAK in the last 2 weeks was $614, while the most expensive was $741.
  • How long should you stay? KAYAK users usually book their hotel in Southold for 1 day.
  • Hotels in Southold offer the best accommodation options for those here to explore the area’s attraction sites while on vacation. Those intending to visit soon should remember that there are various hotels near downtown Southold. Book a room at Southold Beach Motel to conveniently experience these landmarks.
  • If you’re visiting with your companion and want a perfect hideout to rekindle your dimming flame, you’ll have multiple spaces to choose from once you step out of your hotels in Southold. These facilities sit within reach of scenic spots such as Croteaux Vineyards, where you’re sure to taste your favorite brand of wine. Shorecrest Bed and Breakfast is a hotel that puts you near this winery.
  • Suppose you’re here on a weekend getaway with the little ones; remember that Southold features a wide range of fantastic attractions for the whole family to enjoy. For instance, an afternoon at Kenney's Beach where the little ones will relish every moment beachcombing or sunbathing. Reserve a room at the A Walk in the Woods Bed and Breakfast while touring this region.
  • The best time to exploit Southold’s vast outdoors is to stop here in the summer when the prevailing warm weather allows you to venture into the area’s activities comfortably. The Custer Institute Observatory is a good spot for star gazing. A room at the White Blossom House Inn puts you in a great position to get a glimpse of Saturn’s rings.
  • Business executives passing through Southold will be glad to know that the area has many hotels with ideal setups to conduct your business errands. Most of these facilities are a short distance from the city center where the corporate offices are located. Jake's 58 Hotel & Casino is one such hotel.

FAQs when booking a hotel in Southold

  • Where is the best place to stay in Southold, close to dining options?

    Southold’s food and dining scenes are a significant reason why visitors keep returning to this area. With most of the hotels close to the area’s famous restaurants, you’ll have numerous options when sampling the delectable dishes that define this area. Such eateries include Wednesday's Table, Michelangelo Southold, and Latin Fuzion Restaurant. Sleep at Hilton Garden Inn Islip/MacArthur Airport is a hotel around these diverse dishes.

  • What are the best hotels in Southold for hiking and cycling?

    Clarion Hotel & Conference Center is within reach of numerous trails worth considering if you’re a biking or hiking enthusiast. From Pine Meadow to Cascade Mountain and Mount Marcy, there’s every level for all ages and abilities. Step out of your hotel and trek the beaten paths amid beautiful views.

  • Which neighborhood in Southold is best for enjoying the city’s art scene?

    La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport or Hampton Inn Long Island-Brookhaven are two hotels adjacent to the museums and galleries that preserve Southold’s culture and traditions. Stroll through the Southold Historical Museum to learn more about the area’s rich heritage.

  • Which neighborhood in Southold has the best nightlife?

    Fun in Southold doesn’t stop when darkness sets in as the various entertainment joints such as clubs and lounges provide a mellow and indulging atmosphere. Hampton Inn Long Island-Islandia and Rodeway Inn MacArthur Airport are two hotels that let you enjoy the area’s vibrant scene.

  • What are the best hotels near Custer Observatory?

    Travelers who like staying near Custer Observatory recommend White Blossom House Inn.

  • How much does a hotel cost in Southold?

    KAYAK users have found double rooms in Southold for as cheap as $281 in the last 3 days. The average price is $691.

  • How do I find a hotel in central Southold?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Southold districts. You can also do a search using the city map to choose a specific location, like Southold city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Southold hotels with free parking?

    There are many hotels in Southold that offer both parking and free parking. Popular choices among KAYAK users include Holiday Inn Long Island - Islip Arpt East, La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport and Greenporter Hotel.

Where to stay in Southold?

Our map will help you find the perfect place to stay in Southold by showing you the exact location of each hotel.