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Our top choices for Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (245 reviews)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is CA $209
CA $239 total
includes taxes & fees
Mar 24 - Mar 25
The Shoals Suites and Slips

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (620 reviews)
"The hotel was exceptional! We love staying at soundview during the winter months! "
United States
Christina
The price is CA $191
CA $257 total
includes taxes & fees
Mar 23 - Mar 24
Sound View Greenport

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (148 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
The price is CA $261
CA $299 total
includes taxes & fees
Mar 19 - Mar 20
Silver Sands Motel & Beach Bungalows

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (574 reviews)
"Room was beautiful and everyone who worked there was very nice. We’d love to go back! "
United States
Mary
The price is CA $184
CA $249 total
includes taxes & fees
Mar 22 - Mar 23
The Harbor Front Inn

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (177 reviews)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
The price is CA $357
CA $463 total
includes taxes & fees
Mar 17 - Mar 18
The Menhaden

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
The price is CA $431
CA $493 total
includes taxes & fees
Mar 22 - Mar 23
Vine & Sand

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (738 reviews)
"Room was spotless, staff were great and the resort is top notch!!"
United States
Carrie
The price is CA $525
CA $719 total
includes taxes & fees
Mar 30 - Mar 31
Gurney's Montauk Resort & Seawater Spa

Hotel Moraine

Hotel Moraine
2.0 star property
Greenport
9.8 out of 10, Exceptional, (22 reviews)
"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."
United States
Amy
Hotel Moraine

The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (13 reviews)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and Breakfast

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (584 reviews)
"Lovely hotel, very clean and friendly! Definitely going back!"
United States
Hollie
The price is CA $281
CA $321 total
includes taxes & fees
Mar 17 - Mar 18
Sag Harbor Inn

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is CA $238
CA $331 total
includes taxes & fees
Mar 17 - Mar 18
Cliffside Resort Condominiums

Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast
3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12 reviews)
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "
United States
Andrea
Harbor Knoll Bed & Breakfast

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
West Neck Guesthouse

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
United States
steve
Stirling House Bed & Breakfast

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (198 reviews)
"Very nice and very clean."
United States
Daniel
The price is CA $295
CA $392 total
includes taxes & fees
Mar 18 - Mar 19
American Beech Hotel

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (299 reviews)
"Quiet yet situated right in the heart of Greenport."
United States
Andrew
The price is CA $444
CA $508 total
includes taxes & fees
Mar 17 - Mar 18
Zey Hotel

Greenporter Hotel

Greenporter Hotel
2.0 star property
Greenport
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
Greenporter Hotel

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (57 reviews)
"We liked the areas for sitting outside, to sit with a coffee, talk and relax. It was convenient to have a fridge. A very different accommodation but typical for the island. We enjoyed our stay!"
United States
James
Shelter Island House

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (37 reviews)
"A cozy room with great pillows and quiet. Perfect little place. "
United States
Neal
The Chequit
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.
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Stay near popular Southold attractions

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.

Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

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Find out more about Southold

Top reasons to visit Southold

  • Picturesque Beaches: Southold features stunning sandy shores, perfect for relaxing or enjoying a family day by the water.
  • Outdoor Adventures: Engage in various activities like paddleboarding in the summer or skiing in the winter.
  • Local Culture: Explore charming spots like the Southold Fish Market for a taste of local flavours.
  • Scenic Picnic Areas: Enjoy beautiful picnic spots amidst Southold's natural beauty.
  • Diverse Accommodations: Choose from a range of lodging options, including family-friendly and pet-friendly stays.

Find great hotels near Southold

Southold, New York, offers a diverse array of accommodations to cater to every traveller's needs, from family-friendly stays to pet-friendly options. Notably, the Southold Beach Motel stands out for its charming atmosphere and proximity to the stunning shoreline. Whether you're seeking adventure or a relaxing getaway, you'll find the perfect lodging to enhance your experience in this picturesque coastal town.

  • Sound View Greenport: Nestled along the picturesque shoreline, Sound View Greenport offers a delightful blend of beachside relaxation and family-friendly amenities. This 3.5-star hotel is perfect for those looking to unwind by the water while enjoying a range of activities suitable for all ages. With direct beach access, you can soak up the sun or partake in water sports. Business travellers will appreciate the well-equipped meeting rooms and conference space, while families can take advantage of amenities designed for children, including free cribs and window guards for added safety.
  • Sag Harbor Inn: Located a short drive from Southold, Sag Harbor Inn is an excellent choice for business travellers seeking a tranquil environment. This 3.5-star hotel is designed with professionalism in mind, offering essential business amenities including a meeting room that caters to corporate needs. The hotel's serene surroundings provide a peaceful atmosphere, allowing you to focus on your work while enjoying the charm of Sag Harbor. Guests have noted the attentive service and comfortable accommodations that make this inn a reliable option for business trips.
  • The Harbor Front Inn: The Harbor Front Inn stands out as a pet-friendly haven for travellers wanting to bring their furry companions along. This 3.5-star hotel, conveniently located near Southold, combines business amenities with a welcoming atmosphere for pets. With policies that allow dogs and service animals, you won't have to leave your pet behind. Business travellers can benefit from a range of facilities designed to cater to their needs, while enjoying the unique experience of a waterfront stay. Guests have praised the incredible location and accommodating staff, ensuring a comfortable visit for both you and your pet.

Where to stay near Southold

Southold, New York, offers an idyllic vacation experience perfect for outdoor enthusiasts and couples alike. With its stunning beaches and beachfront locations, it's an ideal beach getaway for families and those seeking relaxation. Nearby attractions provide a blend of scenic beauty, historical charm, and luxury excursions. Whether you're enjoying sunny weather or planning a weekend escape, Southold promises a delightful atmosphere for every traveller.

  • Hamptons: Located a mere 16.1km from Southold, the Hamptons are a quintessential summer destination known for their beautiful beaches and upscale charm. This area sees a peak in visitors from June to August, attracting those seeking a beach , outdoor , and romantic experience. With golf courses, music concerts, and luxurious resorts, there’s no shortage of activities to indulge in. Additionally, the picturesque local landmarks, including family-friendly beaches and serene lakes, make the Hamptons a perfect getaway for relaxation and recreation.
  • Greenport: Just 6.4km away from Southold, Greenport is a charming city that offers a delightful mix of outdoor activities and romantic vibes. Like the Hamptons, Greenport experiences peak travel from June to August, drawing visitors who enjoy beaches and local events. Golf courses and music concerts abound, providing ample entertainment options. The proximity to beautiful beaches and event conference venues adds to Greenport’s appeal, making it a must-visit for those looking to experience the coastal lifestyle.
  • Sag Harbor: Located 12.9km from Southold, Sag Harbor is a picturesque city that perfectly encapsulates a coastal retreat. The area enjoys a moderate influx of visitors, especially from June to August, who come for its outdoor , beach , and romantic experiences. From golf courses to ski fields, the range of activities is impressive. Sag Harbor is also home to beautiful beaches, family parks, and scenic spots, making it an ideal location for both adventure and relaxation.

Things to do near Southold

Southold, New York, is perfect for a romantic and outdoor getaway, offering a variety of activities. Enjoy relaxing beach days on the sandy shores, have a picnic in scenic areas, or soak up the sun on the terrace. For the adventurous, paddleboard rentals are available, and there are opportunities for winter sports like skiing. Additionally, music concerts provide entertainment options, making Southold an ideal vacation destination.

Shopping

In Southold, visit the Greenport Farmers' Market, only 6.4km away, for fresh produce and local crafts. The Style Bar and BookHampton, both 12.9km away, offer unique fashion and books. If you're up for a drive, check out larger malls in nearby towns for more extensive shopping options.

Recreation

Goldsmith's Inlet Park offers a tranquil escape with its calming natural surroundings, perfect for relaxation and rejuvenation. For those seeking sport and outdoor fun, Noyac Golf Club provides a beautiful golf experience, while Shelter Island Whale's Tail mini-golf promises family-friendly adventure in a delightful setting.

Adventure

Experience thrilling water rides at Splish Splash Water Park, located 30.6km from Southold, perfect for family fun. For adrenaline junkies, Riverhead Raceway offers exciting motor racing action, situated 29.0km away. Don't miss the scenic Walking Dunes Trailhead, 33.8km from Southold, for a picturesque hiking adventure.

Nightlife

Experience the charm of the Greenport Carousel, just 6.4km away, offering a whimsical outdoor vibe. For a touch of culture and romance, head to Bay Street Theatre, 12.9km from Southold, or Guild Hall, 16.4km away, both perfect for family entertainment.

*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 drop. Tuesdays tend to be the least expensive days to stay, while Saturdays are pricier. Use Expedia's search tool to find budget-friendly hotels by sorting prices from lowest to highest and filtering for eco-friendly options. Additionally, you can save by booking a package that combines your hotel, flights, and activities. Exploring the area on foot is a great way to enjoy free activities while keeping transport costs down.

  • 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: Expedia’s search tool enables you to specify your budget, preferred destination, and additional criteria. You can arrange your search results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Furthermore, you have the option to narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly accommodations that you can book.
  • Consider bundling your trip: You can potentially save some money by combining your Southold hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Southold

Southold, New York, is perfect for outdoor enthusiasts and romantic getaways, offering a blend of beach experiences, cultural attractions, and history. Visitors can enjoy the scenic Southold Town Beach and explore local gems like the Southold Fish Market. The area caters to those seeking relaxation by the shore, engaging outdoor activities, and a taste of local culture, making it an ideal destination for a memorable vacation.

  • 67 Steps Beach: Located 8.0km from Southold, 67 Steps Beach offers a delightful seaside experience with its picturesque views and relaxing beach vibes. It's perfect for sunbathing, swimming, and enjoying the tranquil sounds of the waves.
  • Railroad Museum of Long Island: Just 6.4km away, this cultural gem showcases the rich history of Long Island's railroads. Explore fascinating exhibits and learn about the region's transportation heritage in a family-friendly environment.
  • Sag Harbor Marine Park: Situated 12.9km from Southold, this marina is ideal for outdoor enthusiasts. Enjoy various water activities, unwind on the beach, and take in the scenic beauty of the surrounding area for a perfect adventure.

Best time to go to Southold

The best time to visit Southold is dependant 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

For your visit to Southold, New York, you have several airport options. Islip, NY (ISP-MacArthur) is located 64.4km away, with nearby hotels such as the 3.5-star Hyatt Regency Long Island, Jake's 58 Casino Hotel, and Radisson Hotel Hauppauge, each offering convenient access to the airport. New Haven, CT (HVN-Tweed - New Haven Regional) is 45.1km distant, featuring 4-star accommodations like The Blake Hotel and Graduate by Hilton New Haven. East Hampton, NY (HTO) is the closest at 19.3km, with luxurious options such as the 5-star Mill House Inn and the 4.5-star Topping Rose House, ensuring a comfortable stay while being near the airport.

Frequently asked questions

What is the best area to stay in Southold?
The best area to stay in Southold is the village centre, particularly along Main Road (Route 25) and its immediate side streets.

This area is the heart of Southold, offering a blend of historic charm and modern conveniences. You'll find a selection of local shops, eateries, and a relaxed atmosphere. The village green and the historic Southold Presbyterian Church are central landmarks, and it's quite walkable for exploring the local businesses.

Couples looking for a relaxing escape will appreciate staying in the village centre. It offers easy access to local vineyards, farm stands, and beaches, allowing for leisurely days of wine tasting and coastal strolls. Many of the guesthouses and boutique hotels here provide a comfortable and private setting.

For families, staying near the village centre is also a good option due to its proximity to family-friendly activities. Beaches like Kenney's Beach are a short drive away, offering opportunities for swimming and picnicking.
What are the best hotels in Southold that travellers recommend?
Two of the best hotels in Southold that receive consistently high recommendations from travellers are The Shoals Suites and Slips and Vine & Sand.

The Shoals Suites and Slips is a 3.5-star hotel with an outstanding 9.6 rating. Guests frequently compliment the beautiful and clean rooms, the super comfortable beds, and the nice staff who make them feel welcome. The hotel also features a vineyard with a tasting room and offers private winery tours.

Another highly recommended option is the 3-star Vine & Sand, which also has a 9.6 rating. This hotel is praised for its lovely rooms, which include premium bedding, Egyptian cotton sheets, and rainfall showerheads. Guests can enjoy a free buffet breakfast. It is conveniently located near the Custer Institute and Observatory, just 0.6 km away.
What are the best family hotels in Southold?
For a highly-rated family hotel in Southold, consider The Shoals Suites and Slips.

This 3.5-star hotel, with an impressive 9.6 rating, is an excellent choice for families. Guests consistently praise its clean and new rooms, with the suites often described as beautiful and spacious, featuring super comfortable beds. The staff are noted for being particularly nice and welcoming, ensuring a pleasant stay for all. The hotel also offers cribs free of charge, which is a convenient amenity for those travelling with young children. For adults, there's the added benefit of a vineyard and a winery on-site, offering tasting room experiences, release events, and both private and public tours. The location itself is frequently described as beautiful and great, providing a lovely setting for a family holiday. Find more child-friendly accommodations in Southold
What hotels in Southold offer free breakfast?
For hotels in Southold that offer complimentary breakfast, Vine & Sand is an excellent choice.

The 3-star Vine & Sand, with an impressive 9.6 rating, offers a free buffet breakfast daily, which guests really appreciate. This hotel also provides complimentary Wi-Fi and free self-parking, adding to the convenience. Guests have described the rooms as lovely. It is also conveniently located near the Custer Institute and Observatory, just 0.6 kilometres away, and Sannino's Bella Vita Vineyard, which is 1.5 kilometres from the hotel. Find more hotels with free breakfast in Southold
What are the top pet-friendly hotels in Southold?
For a top pet-friendly hotel in Southold, consider the Cozy Long Island Escape.

This property, with an outstanding 9.6 rating, is superb for those travelling with their beloved canine companions, as it specifically permits dogs. It offers a well-equipped kitchen, a patio, and a secured yard, ensuring both comfort and safety for your pets. Guests also benefit from a deck or lanai, ideal for relaxing outdoors. The Cozy Long Island Escape is conveniently located near the Custer Institute and Observatory, just 1.4 km away, and Horton Lane Beach, a mere 1.7 km distant. See more pet-friendly hotels in Southold
What are the best budget hotels in Southold?
For a highly-rated budget option in Southold, consider Vine & Sand.

The 3-star Vine & Sand, with an exceptional 9.6 rating, offers a fantastic stay with complimentary buffet breakfast and free WiFi. Guests describe the rooms as lovely. It is conveniently located near Custer Institute and Observatory, just 0.6 kilometres away, and Sannino's Bella Vita Vineyard, 1.5 kilometres away. Free self-parking is also available, along with bicycles for guest use. View all budget hotels in Southold
What are the most romantic hotels in Southold for couples?
For couples seeking a romantic getaway in Southold, The Shoals Suites and Slips is an excellent choice.

The 3.5-star Shoals Suites and Slips boasts an impressive 9.6 review rating and offers amenities perfectly suited for couples, including couples dining options and a vineyard on site with a tasting room and private tours. Guests frequently praise its beautiful, clean, and new rooms, the super comfortable beds, and the welcoming staff. Its location is also highly praised, being just 0.7 kilometres from The Old Field Vineyards. See all romantic hotels in Southold
What are the best hotels in Southold near Custer Institute and Observatory?
For hotels in Southold near Custer Institute and Observatory, consider Vine & Sand, or Cozy Long Island Escape.

The 3-star Vine & Sand, rated 9.6, is an excellent choice, being just 0.6 km from the Custer Institute and Observatory. Guests particularly appreciate the lovely rooms and the convenience of free breakfast, including a free buffet breakfast. Free WiFi and free self-parking are also provided.

Another highly-rated option is Cozy Long Island Escape, with a 9.6 rating. This accommodation is 1.4 km from the Custer Institute and Observatory and provides a full kitchen, a patio, and a secured yard, making it ideal for a comfortable stay. It is also 1.7 km from Horton Lane Beach.
When is the best time to go to Southold?
The best time to go to Southold is during the late spring (May to early June) and early autumn (September to early October) when the weather is pleasant, and the area is less crowded.

Late spring offers comfortable temperatures, great for exploring the vineyards and enjoying outdoor activities before the peak summer rush. You'll find most businesses are open, and the roads are less busy, making for a more relaxed experience.

Early autumn is also ideal, with cooler temperatures, stunning foliage, and the grape harvest season in full swing. Many wineries host special events during this time.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Southold.
How can I save on a Southold hotel booking with Expedia?
Members always get our best prices. Find our best Southold hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Southold hotel?
Prices for hotels in Southold often vary, but you can find a great deal from CA $106 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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