Find Romantic Hotels in Southold, NY

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Check availability on Southold Romantic Hotels

Tonight
Jul 30 - Jul 31
Tomorrow
Jul 31 - Aug 1
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Southold Romantic Hotels

The Shoals Suites and Slips
Relax on a bench amidst lush surroundings, with a covered patio just steps away.

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (186)
"Would stay again. So beautiful and clean. "
The price is ₩516,748
₩625,131 total
includes taxes & fees
Jul 31 - Aug 1
The Shoals Suites and Slips
The Roundtree, Amagansett
Enjoy a leisurely ride along the beach, where the ocean meets the shore.

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (89)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is ₩1,799,908
₩2,159,218 total
includes taxes & fees
Aug 10 - Aug 11
The Roundtree, Amagansett
Mill House Inn
Stately home surrounded by lush greenery and mature trees, offering a serene and atmosphere.

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is ₩1,382,941
₩1,738,002 total
includes taxes & fees
Aug 5 - Aug 6
Mill House Inn
The Hedges Inn
Cozy retreat with a four-poster bed, dresser, and nightstand, plus a large mirror and TV for a comfortable stay.

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (70)
"Great staff "
The price is ₩1,249,650
₩1,495,828 total
includes taxes & fees
Jul 31 - Aug 1
The Hedges Inn
EHP Resort & Marina
Experience serene waterfront views and tranquil boating opportunities from the marina.

EHP Resort & Marina

3.5 star property
7.8 out of 10, Good, (8)
"Rooms are well appointed with cozy cottage vibe yet modern and clean . My only ask would be rooms should have one full length mirror. The property is beautiful, location amazing. "
The price is ₩1,085,615
₩1,364,344 total
includes taxes & fees
Aug 4 - Aug 5
EHP Resort & Marina
Topping Rose House
Enjoy a pool and outdoor dining area with lounge chairs and a clear view of the surrounding landscape.

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Great location and very comfortable "
The price is ₩1,745,007
₩1,998,536 total
includes taxes & fees
Aug 12 - Aug 13
Topping Rose House
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.

Top Southold Hotel Reviews

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely hotel. "
Elizabeth 1-night trip
Posted 3 days ago
The Pridwin Hotel

Frequently asked questions

Searching for romantic hotels in Southold?
If you and your partner need a romantic escape, we'd like to help you plan for it. You might consider checking out some of the nearby sights and attractions such as Sparkling Pointe, Croteaux Vineyards, or Osprey's Dominion. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
What's the best hotel for a couple going to Southold?
The Shoals Suites and Slips is a favorite hotel for couples, and features wedding services and free breakfast.
When is the best time of year for a romantic getaway to Southold?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Southold: The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.
What is there to do in Southold?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all there is to see and do in Southold. If you want to spend a day exploring, you might consider a stop at Sparkling Pointe, Croteaux Vineyards, or Osprey's Dominion.
What's the best way to get to Southold and around town during my romantic getaway?
These transportation options in Southold might help your romantic trip get off to a smooth start: Make your way to Southold with a flight to East Hampton, NY (HTO), which is the closest major airport located 11.8 mi (18.9 km) from the city center. If you want to explore the larger area, ride aboard one of the trains from Southold Station.