Best Southold Hotels in 2026 from HK$713 - Fully Refundable Options

A calm lake with a forest in the background during sunset.

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Go beyond your typical stay in Southold

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Hot tub

Condo

Spa

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Our top choices for Southold hotels

Premium bedding, down duvets, laptop workspace

1. The Shoals Suites and Slips

Southold

Connor

HK$2,281

HK$2,803 total

includes taxes & fees

1 Sept - 2 Sept

Private beach, sun-loungers, beach umbrellas, beach towels

Premium bedding, iron/ironing board, free WiFi, individually furnished

2. The Pridwin Hotel

Shelter Island Heights

Anna

HK$4,422

HK$5,558 total

includes taxes & fees

8 Sept - 9 Sept

3. Sound View Greenport

Greenport

Yveline

HK$2,205

HK$3,192 total

includes taxes & fees

9 Sept - 10 Sept

2 bedrooms, iron/ironing board, free WiFi, individually decorated

4. Cliffside Resort Condominiums

Greenport

Christine

HK$2,405

HK$3,447 total

includes taxes & fees

9 Sept - 10 Sept

Premium bedding, minibar, soundproofing, iron/ironing board (on request)

5. Zey Hotel

Greenport

anna

HK$1,906

HK$2,178 total

includes taxes & fees

25 Aug - 26 Aug

Frette Italian sheets, premium bedding, down duvets, pillow-top beds

6. The Harbor Front Inn

Greenport

David

HK$2,168

HK$2,880 total

includes taxes & fees

8 Sept - 9 Sept

7. Shelter Island House

Shelter Island Heights

Dorothy

HK$2,481

HK$2,835 total

includes taxes & fees

19 Aug - 20 Aug

8. The Menhaden

Greenport

Lisa

HK$4,136

HK$5,039 total

includes taxes & fees

30 Aug - 31 Aug

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

9. Oyster Estate

Greenport

Jenny

HK$2,664

HK$3,356 total

includes taxes & fees

7 Sept - 8 Sept

10. North Fork Resort

Greenport

Lisa

HK$2,521

HK$2,880 total

includes taxes & fees

10 Sept - 11 Sept

11. American Beech Hotel

Greenport

kerri

HK$3,097

HK$3,852 total

includes taxes & fees

9 Sept - 10 Sept

12. House on Chase Creek

The Heights

Calvin

HK$1,928

HK$2,202 total

includes taxes & fees

9 Sept - 10 Sept

Frette Italian sheets, premium bedding, Tempur-Pedic beds

13. The Chequit

The Heights

Kristin

HK$2,295

HK$2,622 total

includes taxes & fees

8 Sept - 9 Sept

14. Sag Harbor Inn

Sag Harbor

Christopher

HK$3,687

HK$4,213 total

includes taxes & fees

8 Sept - 9 Sept

Premium bedding, iron/ironing board, free WiFi, bed sheets

15. West Neck Guesthouse

Shelter Island Heights

Allie

HK$2,460

HK$2,810 total

includes taxes & fees

17 Aug - 18 Aug

16. Shorewood Inn

Riverhead

Denise

HK$1,277

HK$1,459 total

includes taxes & fees

17 Aug - 18 Aug

17. The Captain Stannard

Westbrook Center

Jessica

HK$1,835

HK$2,037 total

includes taxes & fees

23 Aug - 24 Aug

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

18. Quality Inn Old Saybrook - Westbrook

Old Saybrook

John

HK$794

HK$913 total

includes taxes & fees

1 Sept - 2 Sept

Desk, iron/ironing board, free WiFi, alarm clocks

19. Spark by Hilton Guilford

Guilford

Michael

HK$830

HK$954 total

includes taxes & fees

30 Aug - 31 Aug

20. Hyatt Place Long Island East End

Riverhead

Anthony

HK$1,561

HK$1,784 total

includes taxes & fees

8 Sept - 9 Sept

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Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)

Sparkling Pointe crafts exquisite sparkling wines using traditional Méthode Champenoise in their Southold vineyard. Savour their diverse bubblies in an elegant tasting room with vineyard views.

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Croteaux Vineyards

10.0/10 (12 reviews)

America's only all-rosé vineyard offers a taste of Provence in New York's North Fork. Savour wine flights in the picturesque garden setting, complete with rustic barn and seaside charm.

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Mattebella Vineyards

8.0/10 (4 reviews)

This family-run vineyard crafts sustainable wines in an intimate North Fork setting. Enjoy personalised tastings with garden-to-table pairings on the patio overlooking lush vines.

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McCabe's Beach

Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.

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Horton Lane Beach

9.0/10 (4 reviews)

This rocky shoreline along Long Island Sound offers peaceful views beside the historic Horton Point Lighthouse. Explore maritime heritage at the adjacent Nautical Museum, open seasonally.

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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)

This intimate vineyard offers personalised expert-guided wine tastings amid sustainable vineyards. Experience their unique White Merlot overlooking scenic North Fork landscapes or stay at their on-site B&B.

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Osprey's Dominion

9.6/10 (5 reviews)

This award-winning North Fork winery showcases sustainable viticulture through distinctive Sauvignon Blanc and Merlot offerings. Enjoy tastings on their spacious lawn with weekend live music and picnic areas.

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The Old Field Vineyards

9.6/10 (5 reviews)

This family-owned vineyard, Long Island's oldest continuously operated winery, offers handcrafted wines in a rustic setting. Enjoy tastings on expansive lawns overlooking Southold Bay.

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Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

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

Top Southold Hotel Reviews

Zey Hotel

10/10 Excellent

"We had a wonderful stay at ZEY Hotel in Greenport! The hotel is absolutely beautiful, with so much charm, character, and a unique boutique feel. The rooms and common areas are beautifully decorated, and the whole property has a warm and relaxing atmosphere. The location is perfect—right in the heart of Greenport and within easy walking distance of the restaurants, shops, waterfront, and everything the village has to offer. We really enjoyed our stay and loved the overall vibe of the hotel. It was the perfect place for a relaxing Greenport getaway. We would definitely stay at ZEY Hotel again and highly recommend"

Water's Edge Resort & Spa

10/10 Excellent

"This is one of our most favorites! The rooms are amazing ( we prefer to spend a little extra for the ocean view). Dinner there is great!. The staff is exceptional."

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"It was a very nice hotel. The room was clean and comfortable, the staff was friendly, and the location was convenient. We had a great stay and really enjoyed our time there."

The Shoals Suites and Slips

10/10 Excellent

"Pretty gosh darn great stay"

Saybrook Point Resort & Marina

8/10 Good

"I have stayed here many times over the past years...I was not knocked out by the overall stay. They call themselves a resort and in a way they are but I question their ability to provide excellent service. On my arrival rgere was no bellman so thr shift manager helped me. When I checked in I was supposed to get a room with garden view and a queen bed. The first room that they gave me was windowless and very small. I was paying 800 a night for my room.and it was a mandatory 2 mights. Room service breakfast was 50 dollars and a drink( bloody mary) and a diet coke was 36. As for the pool there are no chairs because people can use a pool membership even if they weren't staying. I paid for it but there was no chair. The house phone doesn't work. I reported it to the front desk but nothing happen. The nicest and most helpful person was the bell man and the Friday manager. The feeling of comfort a attention seems to be taking a bavk seat By the way I also hosted a dinner at fresh salt...the restaurant on premise...that was perfect and the service was excellent. Maybe the desk should be trained by the resto front of house"

The Harbor Front Inn

10/10 Excellent

"Perfect location, Clean property with water views, and has a pool. Our room had a balcony which was so nice on a beautiful day while taking a break from it all. The room was very spacious and the front desk staff were very nice. Would stay there again in a heart beat."

Greenview Inn Riverhead

8/10 Good

"The rooms were very clean air conditioner works well there's alot of parking .The bathroom was very clean but there was no doors so the whole place was wet"

Hyatt Place Long Island East End

8/10 Good

"👍"

The Atlantic Hotel

10/10 Excellent

"Great location, nice pool,"