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

Southold Hotels

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Oct 6 - Oct 7
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Oct 7 - Oct 8
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Oct 9 - Oct 11
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Oct 16 - Oct 18

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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
P12,642
P16,010 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
P12,010
P15,510 total
includes taxes & fees
Nov 2 - Nov 3
Sound View Greenport

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
P17,577
P20,082 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
P10,091
P13,318 total
includes taxes & fees
Nov 1 - Nov 2
The Harbor Front Inn

5. Zey Hotel

Zey Hotel
Greenport
United States
Renee
P10,571
P12,077 total
includes taxes & fees
Oct 12 - Oct 13
Zey Hotel

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
P10,611
P19,088 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums

7. The Menhaden

The Menhaden
Greenport
United States
Lisa
P24,048
P29,980 total
includes taxes & fees
Nov 1 - Nov 2
The Menhaden

8. North Fork Resort

North Fork Resort
Greenport
United States
Harold
P16,687
P19,065 total
includes taxes & fees
Oct 8 - Oct 9
North Fork Resort

9. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
P12,606
P14,402 total
includes taxes & fees
Oct 12 - Oct 13
Shelter Island House

10. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
P15,710
P20,454 total
includes taxes & fees
Oct 12 - Oct 13
American Beech Hotel

11. The Chequit

The Chequit
The Heights
United States
Patrick
P9,349
P10,681 total
includes taxes & fees
Nov 1 - Nov 2
The Chequit

12. Oyster Estate

Oyster Estate
Greenport
United States
Allison
P15,284
P19,257 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate

13. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
P13,748
P15,707 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn

14. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
P11,580
P13,230 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek

15. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
P25,651
P32,237 total
includes taxes & fees
Nov 2 - Nov 3
Faraway Sag Harbor

16. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
P9,020
P10,306 total
includes taxes & fees
Oct 13 - Oct 14
The Bentley Hotel Southampton

17. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Susan
P9,459
P10,807 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Long Island East End

18. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
P39,181
P44,984 total
includes taxes & fees
Oct 12 - Oct 13
Topping Rose House

19. Shorewood Inn

Shorewood Inn
Riverhead
United States
Heather
P5,356
P6,119 total
includes taxes & fees
Oct 8 - Oct 9
Shorewood Inn

20. Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG
Riverhead
United States
LUIS
P8,161
P9,324 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Express & Suites Riverhead - Long Island by IHG
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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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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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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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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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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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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 coastal landscape with a sunset, a marina, and a residential area.

Top Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 3 hours ago
Hyatt Place Long Island East End
Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Excellent service, clean room, humble and polite receptionist and waited until late for an late check in. Will definitely comeback 💯"
Aurora 1-night trip
Posted 4 hours ago
Greenview Inn Riverhead
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Awesome view! Nice Room! We will come back."
Orapin 1-night trip
Posted 10 hours ago
Sound View Greenport
The Hampton Maid

The Hampton Maid

10/10 Excellent
"excellent stay...staff was friendly. will stay here again."
Joshua 1-night trip
Posted 12 hours ago
The Hampton Maid
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"The rooms have recently been renovated and are very well designed."
Frank 1-night trip
Posted 14 hours ago
The Bentley Hotel Southampton
The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
Antrii 1-night trip
Posted 1 day ago
The Harbor Front Inn
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"This place was great! The restaurant was delicious, the lounge was great, the room was amazing and to top it off the view from our hotel was incredible. The staff were so generous and accommodating. We went for a long weekend/anniversary celebration. I wish we stayed longer and took advantage of the rest of the amenities the hotel has to offer. We will definitely go back."
Ryan 2-night trip
Posted 1 day ago
Saybrook Point Resort & Marina
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great stay. The hotel was clean and convenient. Highly recommend."
Bryan 1-night trip
Posted 2 days ago
Hilton Garden Inn Riverhead
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Friendly staff. Convenient location."
Rodhmir 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

More cheap stays in Southold

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
P5,111
P5,878 total
Oct 12 - Oct 13
includes taxes & fees
8/10 Very Good! (1,000 reviews)
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
P5,575
P6,369 total
Oct 8 - Oct 9
includes taxes & fees
6.8/10 (894 reviews)
Budget Host East End
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
P5,591
P7,953 total
Oct 28 - Oct 29
includes taxes & fees
The Atlantic Hotel
Greenview Inn Riverhead

Greenview Inn Riverhead

1433 W Main St Riverhead NY
P7,220
P8,249 total
Nov 1 - Nov 2
includes taxes & fees
7.4/10 Good! (884 reviews)
Greenview Inn Riverhead
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
P9,020
P10,306 total
Oct 13 - Oct 14
includes taxes & fees
9.6/10 Exceptional! (596 reviews)
The Bentley Hotel Southampton
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
P13,248
P15,136 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (799 reviews)
The Hampton Maid

Find out more about Southold

Top reasons to visit Southold

  • Stunning Beaches: Southold boasts picturesque beaches, perfect for sunbathing and relaxing by the water.
  • Historic Attractions: Visit the Southold Historical Museum to delve into the area's rich history and cultural heritage.
  • Scenic Golf Courses: Enjoy a round of golf amidst beautiful landscapes, ideal for both enthusiasts and casual players.
  • Charming Wineries: Experience delightful winery tours, sampling local wines in a serene setting.
  • Outdoor Activities: Explore numerous recreational areas, offering opportunities for hiking, cycling, and picnicking.

Find great hotels near Southold

Southold offers a delightful selection of accommodation options, perfect for every type of traveller. From charming agritourism properties to well-appointed hotels, you'll find a range of facilities to accommodate families, adventurers, and pet owners alike. Whether you're seeking spacious suites or comfortable hotel rooms, Southold's best hotels promise a memorable stay amidst its picturesque surroundings.

  • Sound View Greenport: Situated merely 5km from Southold, Sound View Greenport is a delightful 3.5-star hotel that offers a serene beachside retreat, ideal for families and pet lovers alike. With a guest rating of 8.4 out of 10, the hotel boasts direct beach access, allowing visitors to indulge in sun-soaked days by the water. Families will appreciate amenities designed for children, including complimentary cribs and safety features like Window Guards. Additionally, the hotel’s pet-friendly policy makes it easy for guests to bring along their furry companions, ensuring a relaxed atmosphere for all.
  • Sag Harbor Inn: Located 13km from Southold, Sag Harbor Inn is a sophisticated 3.5-star establishment, earning an impressive guest rating of 9.4 out of 10. This hotel caters predominantly to business travellers seeking a comfortable stay with modern conveniences. With its elegant design and proximity to local business hubs, it offers a tranquil environment for productivity. Guests can benefit from amenities tailored to corporate needs, ensuring a seamless blend of work and relaxation during their visit.
  • The Harbor Front Inn: Just 6km from Southold, The Harbor Front Inn is a charming 3.5-star hotel that welcomes both business and leisure travellers, achieving a commendable guest rating of 8.8 out of 10. This pet-friendly accommodation features essential amenities for a comfortable stay, including provisions for dogs and a pet policy that prioritises guest convenience. The inn's scenic location by the water provides a picturesque backdrop for relaxation, making it a splendid choice for those desiring a blend of work and leisure.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures, romantic getaways, and entertainment options, making it perfect for any traveller. Explore the charming scenery and family-friendly atmosphere, while enjoying excursions to nearby historical sites. Whether you're basking in sunny weather or indulging in luxury experiences, Southold and its surrounding areas promise an unforgettable vacation, rich in both natural beauty and cultural charm.

  • Hamptons: Nestled approximately 16km from Southold, the Hamptons is a renowned getaway that offers a blend of picturesque beaches, charming towns, and luxurious experiences. The area draws a moderate number of travellers, particularly during the summer months from June to August, making it a vibrant destination for both relaxation and adventure. Visitors can indulge in outdoor activities, enjoy romantic beach strolls, or explore the local golf courses. Notable attractions include the stunning family-friendly beaches and serene lakes, ideal for picnics and leisurely afternoons.
  • Greenport: Located about 6km away from Southold, Greenport is a delightful town that embodies the spirit of coastal living. With a seasonal influx of visitors peaking from June to August, this charming locale is perfect for those seeking outdoor adventures, romantic escapades, and beach fun. Greenport is home to various recreational areas and hosts lively music concerts, offering a taste of local culture. Travellers can explore its beautiful beaches, family-friendly parks, and quaint shops, making it a perfect spot for a leisurely day out.
  • Sag Harbor: Situated 13km from Southold, Sag Harbor is a picturesque village that captivates visitors with its historic charm and vibrant arts scene. The area experiences a seasonal ebb and flow of tourists, peaking in the summer months, and is celebrated for its outdoor activities and stunning beaches. Whether it's golfing, skiing, or simply enjoying the scenic lakes and family beaches, Sag Harbor offers a range of experiences for all ages. The town's quaint streets are lined with unique boutiques and eateries, making it a delightful stop on your journey.

Things to do near Southold

Shopping

In Southold, you can explore local boutiques for unique gifts and souvenirs. If you're up for a drive, consider visiting the Tanger Outlets in Riverhead for a wider selection of brands, or head to the Greenport Village shops for charming, locally crafted items.

Recreation

Greenport Wellness offers rejuvenating yoga classes and holistic therapies in a peaceful setting, promoting relaxation and mindfulness. Nearby, the Southold Bay Community Farm provides a tranquil environment for workshops on sustainable living, cultivating a deeper connection with nature through gardening and organic practices.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 29km from Southold. Feel the adrenaline as you watch high-speed races in a vibrant atmosphere. Alternatively, visit Waterford Speedbowl, situated 43km away, where the excitement of competitive racing awaits.

Nightlife

In Southold, The North Fork Table & Inn offers a charming atmosphere with fine dining and a relaxed bar scene. The Long Island Wine Country hosts various vineyards where you can enjoy wine tastings and live music, creating a delightful evening experience amidst scenic landscapes.

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

Booking tips and Expedia advantages for Southold

To save money on your trip to Southold, consider visiting between January and March when accommodation prices are lower, particularly on Tuesdays, the cheapest day to stay. Avoid Saturdays, which are the priciest. Use Expedia’s search tool to filter by budget and explore package deals that combine hotels, flights, and activities for greater savings. Don't forget to compare room rates and look for exclusive discounts. Additionally, take advantage of free activities and utilise public transport to keep costs down while exploring the area.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Southold are January to March, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Southold is Tuesday. The most expensive day to stay in Southold is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and type of accommodation you wish to stay in. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Southold hotel reservation with your flights and activities by opting for an Expedia package.

Find the best attractions in and around Southold

Southold is an ideal destination for outdoor enthusiasts and those seeking a romantic getaway, offering a blend of entertainment and cultural experiences. Key attractions include the picturesque beaches, Southold Bay, and the Southold Historical Museum, making it perfect for travellers interested in history and outdoor activities. Whether you're exploring its charming urban parks or soaking up the local culture, Southold promises a delightful holiday experience.

  • McCabe's Beach: Experience the relaxed atmosphere of McCabe's Beach, a lovely spot within Southold. Enjoy sunbathing on the sandy shores, swimming in the refreshing waters, or simply taking in the stunning views of the coastline. The beach vibes here create an ideal setting for relaxation and leisure.
  • Safe Harbor Stirling: Located 8km from Southold, Safe Harbor Stirling offers picturesque scenery alongside its serene harbour. With its beautiful views and tranquil setting, it’s an excellent place for a leisurely stroll or enjoying the natural beauty of the waterfront.
  • Old House Museum: A short distance of 8km from Southold, the Old House Museum immerses visitors in local history and culture. Explore its intriguing exhibits that showcase the heritage of the area, making it a delightful stop for those interested in learning more about the region's past.

Best time to go to Southold

The best time to visit Southold is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

Accessing Southold, New York, is convenient via three major airports. John F. Kennedy International Airport (JFK) is situated 124km away, with nearby hotels such as The William Vale and Arlo Williamsburg, both 18km from the airport. Newark Liberty International Airport (EWR) is 153km from Southold, offering luxurious options like The Dominick and Four Seasons Hotel New York Downtown, both 14km from EWR. LaGuardia Airport (LGA) is located 126km away, with excellent accommodations such as Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, both within 10km of the airport. Each airport provides various transportation services for easy access to your hotel.

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 Pier Blue Inn Old Saybrook - Essex and Water's Edge Resort & Spa. See all available top hotels, or 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.
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.
What are some accommodations with pools in Southold?
Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport and The Atlantic Hotel are a couple of other choices that feature an onsite pool. View all hotels with pools in Southold.
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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