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

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Our top choices for Southold hotels

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
¥31,002
¥39,259 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

2. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
¥77,873
¥97,867 total
includes taxes & fees
Sep 14 - Sep 15
The Pridwin Hotel

3. Zey Hotel

Zey Hotel
Greenport
United States
Renee
¥25,922
¥29,615 total
includes taxes & fees
Sep 14 - Sep 15
Zey Hotel

4. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
¥36,725
¥46,346 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Michael
¥36,358
¥45,927 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
¥49,424
¥56,467 total
includes taxes & fees
Oct 14 - Oct 15
Silver Sands Motel & Beach Bungalows

7. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
¥46,065
¥52,631 total
includes taxes & fees
Sep 15 - Sep 16
North Fork Resort

8. The Menhaden

The Menhaden
Greenport
United States
Lisa
¥56,639
¥70,854 total
includes taxes & fees
Sep 15 - Sep 16
The Menhaden

9. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Michael
¥15,538
¥17,868 total
includes taxes & fees
Oct 4 - Oct 5
Quality Inn Old Saybrook - Westbrook

10. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Carolyn
¥12,533
¥14,413 total
includes taxes & fees
Sep 17 - Sep 18
Pier Blue Inn Old Saybrook - Essex

11. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
¥44,381
¥64,399 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums

12. Clinton Motel

Clinton Motel
Clinton
United States
Selena
¥11,982
¥13,779 total
includes taxes & fees
Sep 14 - Sep 15
Clinton Motel

13. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
Clinton
United States
Steven
¥10,599
¥12,189 total
includes taxes & fees
Sep 21 - Sep 22
Lamplighter Motel - Clinton, Connecticut

14. Spark by Hilton Guilford

Spark by Hilton Guilford
Guilford
United States
Stacy
¥17,634
¥20,279 total
includes taxes & fees
Sep 21 - Sep 22
Spark by Hilton Guilford

15. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
¥48,614
¥61,253 total
includes taxes & fees
Oct 7 - Oct 8
Oyster Estate

16. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
¥47,742
¥60,689 total
includes taxes & fees
Sep 21 - Sep 22
American Beech Hotel

17. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
¥30,914
¥35,318 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House

18. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
¥33,069
¥37,782 total
includes taxes & fees
Oct 5 - Oct 6
House on Chase Creek

19. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
¥48,157
¥55,020 total
includes taxes & fees
Sep 15 - Sep 16
West Neck Guesthouse

20. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
¥49,770
¥56,862 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn
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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. Savor 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. Savor wine flights in the picturesque garden setting, complete with rustic barn and seaside charm.
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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)
This intimate vineyard offers personalized 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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Horton Point Park

9.4/10 (3 reviews)
This 1857 lighthouse stands sentinel over Long Island Sound, housing a nautical museum filled with maritime artifacts. Climb to the top for panoramic views, then follow the nature trail to the peaceful rocky beach below.
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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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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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Mattebella Vineyards

8.0/10 (4 reviews)
This family-run vineyard crafts sustainable wines in an intimate North Fork setting. Enjoy personalized tastings with garden-to-table pairings on the patio overlooking lush vines.
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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.

See all hotels in Southold
A pebbled beach at sunset with the sun reflecting on the water.
Photo by Benny Goh

Top Southold Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

8/10 Good
"For a relatively "affordable" ($380!!!) place to stay for one night during the highly in-demand Labor Day weekend on the East End of Long Island, the Greenview Inn was the closest we could get to what we were looking for: A clean bed to lay our heads at the end of a busy wedding reception. Thank goodness we were able to pay with OneKey Cash. The room was relatively clean, and appeared to have been recently renovated. The sheets felt slightly damp, perhaps from humidity, perhaps because they had been insufficiently dried during laundering. Additionally, there were a couple of small flies buzzing about as we tried to get to bed. We were on the first floor, so privacy and noise mitigation were a key concern. The thin curtains barely did the job of covering the front windows, and had to be jury-rigged to ensure that the air conditioner didn't blow them away from the window. Heavier curtains set within the window frame would be a nice upgrade. We did not make much use of any amenities on the premises, so we cannot speak to any on-site coffee or breakfast option. We did appreciate the property's beautiful vista on the Peconic River however. The property's dock is sorely in need of repair or removal, but the waterfront appears to be an unrecognized asset for the property. There should be kayaks/canoes available for guests whether for free or by rental. All in all, grateful for a relatively clean and quiet place to stay the night, but there is absolutely room for improvement."
Christopher 1-night trip
Posted 4 hours ago
Greenview Inn Riverhead
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
Michael 1-night trip
Posted 19 hours ago
Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Deverian actualizar las tv’s"
Maria 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex
The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"This was our first trip to Greenport and we had a fabulous stay. The hotel was perfectly located downtown."
Ken 2-night trip
Posted 2 days ago
The Harbor Front Inn
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"
Nancy 2-night trip
Posted 2 days ago
The Atlantic Hotel
North Fork Resort

North Fork Resort

10/10 Excellent
"This property is so awesome! Adorable cottages, not very big, but sufficient. We were 2 couples, and we managed. Very quaint an comfortable. Services were provided if asked. They give you everything you need. I may buy in or for sure go back as a guest next year. We loved it, and it's so convenient to town, restaurants, and wineries all around you."
LISA 2-night trip
Posted 4 days ago
North Fork Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"Such an amazing hotel to stay for the weekend"
Olivia 1-night trip
Posted 4 days ago
Zey Hotel
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 11 days ago
Faraway Sag Harbor

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
¥12,533
¥14,413 total
Sep 17 - Sep 18
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
¥13,671
¥15,618 total
Sep 14 - Sep 15
includes taxes & fees
Budget Host East End
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT
¥15,538
¥17,868 total
Oct 4 - Oct 5
includes taxes & fees
7.8/10 Good! (1,005 reviews)
Quality Inn Old Saybrook - Westbrook
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
¥18,318
¥24,768 total
Oct 1 - Oct 2
includes taxes & fees
7.2/10 Good! (1,004 reviews)
The Atlantic Hotel
Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG

1707 Old Country Rd Riverhead NY
¥25,038
¥28,605 total
Oct 14 - Oct 15
includes taxes & fees
Holiday Inn Express & Suites Riverhead - Long Island by IHG
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
¥32,488
¥37,119 total
Oct 13 - Oct 14
includes taxes & fees
The Hampton Maid

Find out more about Southold

Top reasons to visit Southold

  • Charming Beaches: Southold boasts beautiful beaches where visitors can relax, swim, and enjoy stunning sunsets.
  • Winery Tours: Experience local flavors by touring the nearby wineries, sampling exquisite wines in a picturesque setting.
  • Rich History: Discover local heritage at the Southold Historical Museum, showcasing the town's fascinating past.
  • Outdoor Activities: Enjoy golfing and exploring recreational areas, perfect for outdoor enthusiasts and nature lovers.
  • Cozy Accommodations: Stay in delightful agritourism properties and charming bed & breakfasts, catering to all traveler preferences.

Find great hotels near Southold

Explore the charming accommodations in Southold, New York, where you can find a variety of lodging options, including delightful agritourism properties and cozy bed & breakfasts. Whether you're seeking adventure, a pet-friendly environment, or a family-friendly experience, Southold's hotels cater to every traveler's needs. With a selection of hotel rooms and suites available, you're sure to find the perfect stay for your vacation.

  • Sound View Greenport: Nestled just 5km from Southold, Sound View Greenport is a charming 3.5-star hotel offering a delightful beach experience. Rated 8.4 out of 10 by guests, this property is ideal for families and business travelers alike. With direct access to the beach, you can enjoy sun-soaked days by the water. The hotel is particularly family-friendly, featuring amenities such as free cribs and window guards for children, ensuring a safe and comfortable stay for your little ones.
  • Sag Harbor Inn: Located 13km from Southold, the Sag Harbor Inn is a stylish 3.5-star lodging with an impressive guest rating of 9.4 out of 10. This hotel caters primarily to business travelers, providing a serene environment for work and relaxation. With its convenient location, guests can easily access local businesses and attractions, making it a practical choice for those on the go. The inn’s pleasant atmosphere and attentive service set the stage for a productive stay.
  • The Harbor Front Inn: Situated 6km from Southold, The Harbor Front Inn is a welcoming 3.5-star hotel with a guest rating of 8.8 out of 10. This property is pet-friendly, accommodating travelers who wish to bring their furry companions along. With a variety of pet amenities, including a waived fee for service animals and specific policies for dogs, this inn ensures a comfortable stay for both you and your pet. The Harbor Front Inn also caters to business travelers, combining convenience with a relaxed atmosphere.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic escapes, perfect for any traveler. Explore its charming neighborhoods, soak up the sunny weather, and enjoy family-friendly excursions. Nearby attractions showcase stunning scenery and rich historical experiences. Whether you're looking for luxury or a quaint atmosphere, Southold embodies the charm of coastal living, making it an ideal destination for an unforgettable vacation.

  • Hamptons: Located 16km away from Southold, the Hamptons are synonymous with luxury and relaxation. This charming destination attracts visitors seeking a mix of beautiful beaches, outdoor activities, and romantic getaways. The area sees a seasonal influx of travelers, especially during the summer months from June to August, when the beaches come alive with sunbathers and water sports enthusiasts. Notable attractions include stunning family-friendly beaches, picturesque lakes, and golf courses that cater to both beginners and seasoned players. Whether you're looking to unwind by the shore or enjoy an active day outdoors, the Hamptons offer a delightful blend of experiences.
  • Greenport: Just 6km from Southold, Greenport is a picturesque village that embodies the charm of the North Fork. Known for its vibrant arts scene and waterfront views, this city welcomes a variety of travelers, particularly during the peak season from June to August. Visitors flock to Greenport for its outdoor adventures, romantic ambiance, and stunning beaches. Spend your day exploring local parks, enjoying music concerts, or indulging in fresh seafood at quaint restaurants. With its friendly atmosphere and scenic beauty, Greenport is perfect for couples and families alike looking to create lasting memories.
  • Sag Harbor: Approximately 13km from Southold, Sag Harbor is a historic whaling village that offers a unique blend of culture and natural beauty. This lively city attracts visitors year-round, peaking in the summer months. Travelers are drawn to Sag Harbor for its outdoor recreation, stunning beaches, and romantic settings. Enjoy activities such as golfing or skiing, and take advantage of the beautiful family-friendly beaches and serene lakes. With its charming shops, art galleries, and rich maritime history, Sag Harbor provides an enchanting experience for all types of visitors.

Things to do near Southold

Shopping

In Southold, explore local shops for unique gifts and souvenirs. If you're up for a drive, visit Tanger Outlets in Riverhead, about 18km away, featuring a variety of brand-name stores and a vibrant shopping atmosphere.

Recreation

In Southold, indulge in rejuvenating treatments at the Spa at East Wind, surrounded by lush gardens. For a serene escape, visit the North Fork Wellness Center, which offers yoga classes and holistic therapies to enhance your mind and body connection.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 29km from Southold, where you can feel the adrenaline rush of fast cars and lively competition. Alternatively, head to Waterford Speedbowl, 43km away, for more exciting races in a vibrant atmosphere filled with sports energy.

Nightlife

In Southold, you can unwind at local wineries like Sparkling Pointe, where you can enjoy wine tastings in a relaxing atmosphere. For a more lively experience, explore nearby Greenport, which boasts charming bars and live music venues, perfect for a fun night out with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Southold

Southold offers a delightful blend of outdoor and romantic activities, perfect for an entertaining vacation. Visitors can explore the scenic Southold Bay and delve into local history at the Southold Historical Museum. The area also features beautiful beaches and urban parks, catering to those seeking cultural experiences and outdoor adventures. Whether you're relaxing by the shore or enjoying the charming local attractions, Southold promises a memorable getaway.

  • The Hamptons Beaches: Located 19km from Southold, The Hamptons Beaches offer an idyllic seaside experience with pristine sands and vibrant beach vibes. Enjoy sunbathing, swimming, and beachside dining while soaking in the picturesque coastal scenery.
  • Orient Point County Park: Also 19km from Southold, Orient Point County Park is an urban park ideal for family outings. With outdoor activities such as hiking and picnicking, visitors can relish the natural beauty of the area while enjoying a peaceful escape from city life.
  • Horton Point Park: Situated within Southold, Horton Point Park features a historic lighthouse that reflects the area's rich maritime culture. Explore scenic trails and enjoy breathtaking views of the Long Island Sound, immersing yourself in the local heritage.

Best time to go to Southold

The best time to visit Southold can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Southold falls in August, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Southold falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighSlightly High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to Southold

Traveling to Southold, New York, is convenient with several major airports nearby. New York, NY (JFK-John F. Kennedy Intl.) is 124km away, with excellent hotels like The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty Intl. Airport (EWR) is 153km away, with luxurious options like The Dominick and Four Seasons Hotel New York Downtown, both 14km from the airport. Lastly, LaGuardia Airport (LGA) is 126km from Southold, featuring upscale hotels such as Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, both within 10km of the airport. These hotels offer easy access to their respective airports for a smooth travel experience.

Frequently asked questions

Where is the best place to stay in Southold?
The Shoals Suites and Slips is one of the top choices for your stay based on our traveler data. This hotel offers a restaurant and private balconies. Other good choices for your trip to the area are Sound View Greenport and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or vacation rentals in Southold.
What's the top vacation rental in Southold?
New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental outside of Southold is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Southold.
If I need to cancel my hotel reservation in Southold, will I receive a refund?
Yes, the majority of room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.
Where can I learn more about changing or cancelling my trip to Southold?
To access more information about rescheduling or cancelling your trip to Southold, head over to our customer service page.
What's the best pet-friendly accommodation in Southold?
White Blossom House Inn is a top hotel for people traveling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. See more pet-friendly hotel accommodations in Southold.
Where is the best hotel to stay near Sparkling Pointe?
White Blossom House Inn is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and private patios. It's located just a short 0.9 mi (1.4 km) from Sparkling Pointe.
What about the best place to stay close to Mattebella Vineyards?
One of the top choices for your stay is White Blossom House Inn, located a short 0.7 mi (1.1 km) from Mattebella Vineyards, and this hotel offers free parking and private patios.
What are some accommodations with pools in Southold?
Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. The Atlantic Hotel and Water's Edge Resort & Spa are a couple of other choices that feature an onsite pool. View all hotels with pools in Southold.
What's the best place to stay near John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
What's it like to stay in Southold?
Visitors can enjoy all that Southold has to offer including the wineries, beaches, and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 141 hotels and other accommodations to choose from. Find out more about Southold.
What should I see while I'm in Southold?
The picturesque setting of McCabe's Beach and Horton Lane Beach exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Sparkling Pointe and Croteaux Vineyards. Check out what more to see and do in Expedia's Southold guide.
How should I get around Southold?
To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.
What's the weather like 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.

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