Find Romantic Hotels in Southold, NY from CA $364

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Check availability on Southold Romantic Hotels

Our top choices for Southold romantic hotels

Dining

American Beech in Greenport - Deluxe King Suite 12

American Beech in Greenport - Deluxe King Suite 12
Greenport
The price is CA $274
CA $417 total
includes taxes & fees
Apr 15 - Apr 16
American Beech in Greenport - Deluxe King Suite 12
Bar (on property)

American Beech in Greenport NY - King Suite 1

American Beech in Greenport NY - King Suite 1
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Perfect Great place"
United States
Dean J.
The price is CA $247
CA $383 total
includes taxes & fees
Apr 15 - Apr 16
American Beech in Greenport NY - King Suite 1
Property grounds

American Beech - Deluxe King 5

American Beech - Deluxe King 5
Greenport
8.6 out of 10, Excellent, (4 reviews)
"I thoroughly enjoyed my stay. I was upgraded before arriving at the hotel and was very pleased with my stay. The staff were kind and accommodating, I will definitely return."
United States
Ayana M.
The price is CA $274
CA $417 total
includes taxes & fees
Apr 15 - Apr 16
American Beech - Deluxe King 5
Dining

American Beech - Deluxe King Suite 14

American Beech - Deluxe King Suite 14
Greenport
10.0 out of 10, Exceptional, (2 reviews)
"Right in the heart of Greenport Villiage "
United States
Suzanne B.
The price is CA $316
CA $474 total
includes taxes & fees
Apr 15 - Apr 16
American Beech - Deluxe King Suite 14
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $233
CA $364 total
includes taxes & fees
Apr 15 - Apr 16
American Beech in Greenport - Petite King Room 7
Property grounds

American Beech in Greenport - Deluxe King Suite 11

American Beech in Greenport - Deluxe King Suite 11
Greenport
The price is CA $274
CA $417 total
includes taxes & fees
Apr 15 - Apr 16
American Beech in Greenport - Deluxe King Suite 11
Property grounds

American Beech - King Suite 2

American Beech - King Suite 2
Greenport
10.0 out of 10, Exceptional, (3 reviews)
"Such a fabulous trip!"
United States
Katherine C.
The price is CA $247
CA $383 total
includes taxes & fees
Apr 15 - Apr 16
American Beech - King Suite 2
Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is CA $993
CA $1,823 total
includes taxes & fees
Apr 18 - Apr 19
Work and Play Special! Extended Stay Discount
Interior

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is CA $1,377
CA $2,313 total
includes taxes & fees
May 7 - May 8
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Property grounds

American Beech in Greenport - Two-Bedroom Apartment 8

American Beech in Greenport - Two-Bedroom Apartment 8
Greenport
The price is CA $550
CA $778 total
includes taxes & fees
Apr 20 - Apr 21
American Beech in Greenport - Two-Bedroom Apartment 8
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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Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

6/10 Okay
"Front desk staff were amazing! The bar staff were very attentive and friendly. Rooms are clean, but definitely dated."
Michelle 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

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 Horton Lane Beach. 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.
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 Horton Lane Beach.
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.

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