Find Romantic Hotels in Southold, NY

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Southold Romantic Hotels

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Top Southold Romantic Hotels

The Shoals Suites and Slips
Garden Suite King | 1 bedroom, premium bedding, down duvets, individually decorated

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (174)
"Third stay here, always a pleasure and so close to my favorite southold vineyards"
The price is £262
includes taxes & fees
7 Jul - 8 Jul
The Shoals Suites and Slips
The Roundtree, Amagansett
Beach nearby, white sand, sun-loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (88)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is £1,138
includes taxes & fees
8 Jul - 9 Jul
The Roundtree, Amagansett
Mill House Inn
Front of property – evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (69)
"Great experience at a wonderful property!"
The price is £916
includes taxes & fees
7 Jul - 8 Jul
Mill House Inn
The Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Absolutely fabulous homely and beautifully decorated Conveniently located between downtown and the beach so easy to walk"
The price is £705
includes taxes & fees
7 Jul - 8 Jul
The Hedges Inn
EHP Resort & Marina
Boating

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 £507
includes taxes & fees
8 Jul - 9 Jul
EHP Resort & Marina
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is £1,158
includes taxes & fees
8 Jul - 9 Jul
Topping Rose House
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Pool

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

9.2 out of 10, Wonderful, (9)
"Great location and comfortable home. Easy check in and check out."
The price is £1,016
includes taxes & fees
7 Jul - 8 Jul
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton Inn
Aerial view

Southampton Inn

3.0 star property
8.6 out of 10, Excellent, (525)
"Such a great find! Close to Cooper’s Beach! Walking distance to shopping and restaurants. Prime location and beautiful sitting area outside. The pool is an added plus."
The price is £376
includes taxes & fees
7 Jul - 8 Jul
Southampton Inn
American Beech in Greenport NY - King Suite 1
Interior

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is £327
includes taxes & fees
23 Jul - 24 Jul
American Beech in Greenport NY - King Suite 1
American Beech - Deluxe King Suite 14
Interior

American Beech - Deluxe King Suite 14

10.0 out of 10, Exceptional, (2)
The price is £376
includes taxes & fees
9 Jul - 10 Jul
American Beech - Deluxe King Suite 14
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.

Frequently asked questions

Searching for romantic hotels in Southold?
If you and your partner need some romantic time away, we've got just the thing. 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 neighbourhood or distance to top landmarks, so you'll be able to see everything on your list.
What's the best place to stay for a romantic holiday to Southold?
The Shoals Suites and Slips is a favourite 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, take a look at these details about year-round temperatures in Southold: The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.
What is there to do in Southold?
There's nothing better than wandering around 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 stopping 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?
This information about transportation options in Southold might help your romantic getaway go off without a hitch: 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 centre. To venture out into the surrounding area, hop aboard a train at Southold Station.