Hotels in Southold

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Where to stay in Southold?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Southold on Hotels.com. These Southold hotels consistently deliver on comfort, location and traveler experience. Last updated on August 19, 2026.

The Shoals Grand Suite | Private kitchen

1. The Shoals Suites and Slips

Southold

CNY1,961

CNY2,409 total

includes taxes & fees

Sep 1 - Sep 2

2. The Pridwin Hotel

Shelter Island Heights

CNY3,603

CNY4,528 total

includes taxes & fees

Sep 13 - Sep 14

3. Cliffside Resort Condominiums

Greenport

CNY2,063

CNY2,957 total

includes taxes & fees

Sep 20 - Sep 21

4. Sound View Greenport

Greenport

CNY1,829

CNY2,667 total

includes taxes & fees

Sep 15 - Sep 16

5. Silver Sands Motel & Beach Bungalows

Greenport

CNY3,164

CNY3,615 total

includes taxes & fees

Sep 20 - Sep 21

Private Suite, 1 King Bed, Non Smoking (Private Suite - Adults Only)

Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking

6. Zey Hotel

Greenport

CNY1,363

CNY1,557 total

includes taxes & fees

Sep 7 - Sep 8

Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

7. The Harbor Front Inn

Greenport

CNY1,863

CNY2,475 total

includes taxes & fees

Sep 8 - Sep 9

8. The Menhaden

Greenport

CNY3,496

CNY4,264 total

includes taxes & fees

Aug 25 - Aug 26

9. Shelter Island House

Shelter Island Heights

CNY2,129

CNY2,432 total

includes taxes & fees

Sep 7 - Sep 8

Suite, 1 King Bed, Kitchenette (Living Room) | Living room

10. West Neck Guesthouse

Shelter Island Heights

CNY2,110

CNY2,411 total

includes taxes & fees

Aug 23 - Aug 24

11. Oyster Estate

Greenport

CNY2,195

CNY2,766 total

includes taxes & fees

Sep 7 - Sep 8

12. North Fork Resort

Greenport

CNY2,163

CNY2,471 total

includes taxes & fees

Sep 17 - Sep 18

13. Sag Harbor Inn

Sag Harbor

CNY2,383

CNY2,723 total

includes taxes & fees

Sep 20 - Sep 21

14. The Chequit

The Heights

CNY1,969

CNY2,250 total

includes taxes & fees

Sep 17 - Sep 18

15. American Beech Hotel

Greenport

CNY2,658

CNY3,305 total

includes taxes & fees

Sep 20 - Sep 21

16. Shorewood Inn

Riverhead

CNY1,098

CNY1,254 total

includes taxes & fees

Aug 23 - Aug 24

Standard Room, 1 Bedroom, Private Bathroom

17. The Captain Stannard

Westbrook Center

CNY1,575

CNY1,748 total

includes taxes & fees

Sep 20 - Sep 21

A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

18. House on Chase Creek

The Heights

CNY1,654

CNY1,890 total

includes taxes & fees

Sep 8 - Sep 9

19. Quality Inn Old Saybrook - Westbrook

Old Saybrook

CNY681

CNY783 total

includes taxes & fees

Sep 20 - Sep 21

20. Hyatt Place Long Island East End

Riverhead

CNY1,322

CNY1,510 total

includes taxes & fees

Sep 9 - Sep 10

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Go beyond your typical stay in Southold

Pet friendly

Pool

Spa

Hot tub

Family friendly

Our prices for hotels in Southold are cheapest in January

Top landmarks in Southold

Sparkling Pointe

8.8/10 (11 reviews)

Travelers might want a tour of Sparkling Pointe, just one of the places to visit, and located 1 mi (1.6 km) from central Southold.

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Croteaux Vineyards

10.0/10 (12 reviews)

Travelers might want a tour of Croteaux Vineyards, just one of the places to visit, and located 1.5 mi (2.4 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.

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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)

Travelers might want a tour of Sannino's Bella Vita Vineyard, just one of the places to visit, and located 2.2 mi (3.5 km) from central Southold. If you enjoy your tour, head to Osprey's Dominion, just a short walk away.

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McCabe's Beach

When the beach is calling your name, you might want to head down to McCabe's Beach, located 1.6 mi (2.5 km) from central Southold. If you want to continue walking by the waves, head to Horton Lane Beach located nearby.

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Horton Lane Beach

9.0/10 (4 reviews)

If you can't wait to get to the beach, you might enjoy a trip to Horton Lane Beach located 1.6 mi (2.6 km) from central Southold. If you want to continue walking by the waves, head to McCabe's Beach located nearby.

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Horton Point Park

9.4/10 (3 reviews)

Horton Point Park is 1.7 mi (2.8 km) from central Southold, why not stop by during your stay. Want to stretch your legs some more? Head to Goldsmith's Inlet Park, located nearby.

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Osprey's Dominion

9.6/10 (5 reviews)

Travelers might want a tour of Osprey's Dominion, just one of the places to visit, and located 1.9 mi (3 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.

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Custer Institute and Observatory

Custer Institute and Observatory is 1 mi (1.6 km) from central Southold, why not stop by during your stay. If you have fun at Custer Institute and Observatory, you'll love Railroad Museum of Long Island and 8 Hands Farm, both located nearby.

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Learn more about Southold

Southold is well-known for its attractions such as Sparkling Pointe and Mattebella Vineyards. The city has something for everyone including sights like Croteaux Vineyards and McCabe's Beach within a sunny setting.

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A pebbled beach at sunset with the sun reflecting on the water.

Check out reviews of Southold hotels guests love

North Fork Resort

10/10 Excellent

"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."

Hyatt Place Long Island East End

10/10 Excellent

"This hotel chain is MY NEW FAVORITE! We had never stayed at a Hyatt Hotel before, but I am so impressed! From the super-friendly staff, cleanliness, modern look, breakfast varieties galore, eating with actual cutlery, not plastic, real cups and plates, not paper, what a treat! I truly felt pampered! The A/C in the room was perfect, and the hot water in the shower was 'so relaxing and soothing!' Great job Hyatt Place Long Island-Riverhead! See you again!"

Sound View Greenport

8/10 Good

"Stayed here for 2 nights mid-August. Pool was nice (could have been a little cleaner). Restaurant, excellent. Valet staff, excellent. Front desk staff, good. Bar, nice. Breakfast included, very nice. Room, a bit dated but nicely renovated. Through the years I always wanted to stay here - glad I did. The view (and sunset) of the Long Island Sound from the shared balcony cannot be beat. Breathtaking."

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Clean and comfortable room. Very dated furniture."

Water's Edge Resort & Spa

8/10 Good

"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."

The Chequit

10/10 Excellent

"Everything was great ! Wish we had been there when restaurant was open."

Hampton's Vacation Inn

10/10 Excellent

"Great place to stay. The closing of the pool at 7pm is a bit early."

Zey Hotel

10/10 Excellent

"James was amazing"

The Hampton Maid

10/10 Excellent

"Wonderful place, room is clean, modern and spacious. Such a nice garden right in front of the rooms, very relaxing atmosphere. Very professional and helpful staff. Great location, close to restaurants. Highly recommend it."

Frequently asked questions

How much does a hotel room cost in Southold?

You can choose a great hotel in Southold from CNY613 with properties to suit all budgets and needs. If you're after an affordable hotel in Southold that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Southold hotels?

Discover great deals on Southold hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Southold hotels.

Can I book Southold hotels with free cancellation?

To book a refundable Southold hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some of the best hotels in Southold for couples?

Stay at a top-rated Southold romantic hotel and make the most of your couple's vacation. Our travelers love The Shoals Suites and Slips, a hotel with a restaurant as well as in-room champagne service. Discover more hotels in Southold on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".

What are the top Southold hotels with a pool?

For some added luxury, discover the best Southold hotels with a pool. Vine & Sand is a great bed & breakfast with a seasonal outdoor pool and a guest rating of 9.8 out of 10. Plus, you can make the most of its free buffet breakfast and free bicycle rentals. You can select "Pool" in the "Amenities" filter of your search on Hotels.com to find even more places to stay in Southold with a pool.

What are some of the best Southold hotels with free parking?

If you're driving, a great Southold hotel with free parking is a bonus. Our travelers' favorites include:

White Blossom House Inn: A hotel with an average guest rating of 10 out of 10
Vine & Sand: A bed & breakfast with an average guest rating of 9.8

What are some popular hotels in central Southold?

For hotels in central Southold, check out The Harbor Front Inn and Silver Sands Motel & Beach Bungalows. Travelers love The Harbor Front Inn for its location, as well as the seasonal outdoor pool, free continental breakfast and 24-hour gym this hotel offers. Silver Sands Motel & Beach Bungalows is another popular central hotel with a private beach, a free beach club and a full-service spa. Pipes Cove and The Heights are some of the most central neighborhoods for your Southold vacation.

What accommodations do travelers recommend in Southold?

Guests like The Shoals Suites and Slips, Vine & Sand and Sound View Greenport.

Can I book refundable accommodations in Southold?

If you want the flexibility to change your travel plans to Southold, most properties offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Southold if I want a vacation home instead of a traditional hotel?

If you want to find a good alternative to a hotel, browse our selection of 118 vacation homes. You can also consider one of the 12 cottages for your trip.

What will the weather in Southold be like during my vacation?

The warmest months in Southold are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.

Why should I book my Southold accommodation with Hotels.com?

There are plenty of reasons to book your Southold travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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Book Hotels in Southold on Hotels.com

Hotels in Southold

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Southold?

1. The Shoals Suites and Slips

2. The Pridwin Hotel

3. Cliffside Resort Condominiums

4. Sound View Greenport

5. Silver Sands Motel & Beach Bungalows

6. Zey Hotel

7. The Harbor Front Inn

8. The Menhaden

9. Shelter Island House

10. West Neck Guesthouse

11. Oyster Estate

12. North Fork Resort

13. Sag Harbor Inn

14. The Chequit

15. American Beech Hotel

16. Shorewood Inn

17. The Captain Stannard

18. House on Chase Creek

19. Quality Inn Old Saybrook - Westbrook

20. Hyatt Place Long Island East End

Go beyond your typical stay in Southold

Price trends for hotels in Southold

Typical weather for Southold

Top landmarks in Southold

Sparkling Pointe

Croteaux Vineyards

Sannino's Bella Vita Vineyard

McCabe's Beach

Horton Lane Beach

Horton Point Park

Osprey's Dominion

Custer Institute and Observatory

Learn more about Southold

Check out reviews of Southold hotels guests love

North Fork Resort

Hyatt Place Long Island East End

Sound View Greenport

Pier Blue Inn Old Saybrook - Essex

Water's Edge Resort & Spa

The Chequit

Hampton's Vacation Inn

Zey Hotel

The Hampton Maid

Frequently asked questions

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