Southold hotels

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Thu 2/9
Mon 2/13
...and more

Good to know

Low season

April

High season

June

Average price (weeknight)

$305

Average price (weekend night)

$418
Cheapest month to stay with an average 40% drop in price.
Most expensive month to stay with an average 64% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Best Southold hotels

Most recommended Southold hotels

Show all
Dering Harbor Inn - Shelter Island - Outdoors view
Free Wi-Fi
Pool
Sound View Greenport - Greenport - Dining room
Sound View Greenport
9.7 Wonderful
$417+
$417+
Parking
Free Wi-Fi
Pool
Pet friendly
$1,401+
Parking
Free Wi-Fi
Pet friendly
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
Airport shuttle
Free Wi-Fi
Pool
Pet friendly
American Beech Hotel
8.7 Very good
$359+
$359+
Parking
Pet friendly

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 April and September.
  • 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 Monday. The opposite is true for, Thursday, which is usually the most expensive day.
  • 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 to stay in Southold?

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