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

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Our top choices for Southold hotels

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $226
CA $298 total
includes taxes & fees
Nov 23 - Nov 24
Sound View Greenport

2. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (348 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is CA $248
CA $319 total
includes taxes & fees
Oct 29 - Oct 30
The Shoals Suites and Slips

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (668 reviews)
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
United States
Antrii
The price is CA $185
CA $251 total
includes taxes & fees
Nov 16 - Nov 17
The Harbor Front Inn

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (439 reviews)
"We had a great experience at the Zey Hotel. Our room was perfect with a cute balcony we could use. The staff was extremely helpful & welcoming. Will definitely stay again!"
United States
sacha
The price is CA $215
CA $245 total
includes taxes & fees
Nov 10 - Nov 11
Zey Hotel

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (184 reviews)
"Everything was immaculate and staff were fantastic. Lots of small details that made the stay especially lovely."
United States
Gaurav
The price is CA $333
CA $381 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows

6. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (128 reviews)
"Wonderful- so charming and comfortable; upscale yet casual"
United States
Ann
The Pridwin Hotel

7. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (73 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is CA $210
CA $240 total
includes taxes & fees
Nov 19 - Nov 20
The Chequit

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $237
CA $426 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums

9. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very good, (875 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is CA $498
CA $682 total
includes taxes & fees
Nov 10 - Nov 11
Gurney's Montauk Resort & Seawater Spa

10. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (193 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is CA $461
CA $582 total
includes taxes & fees
Nov 8 - Nov 9
The Menhaden

11. Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (21 reviews)
"The owners are the sweetest people! Location is great, our room exceptionally clean, pool great, and amenities fantastic! I look forward to returning."
United States
yohanny
Vine & Sand

12. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,008 reviews)
"Beautiful setting, good food, friendly staff. Will definitely stay again"
United States
cynthia
The price is CA $250
CA $311 total
includes taxes & fees
Nov 1 - Nov 2
Water's Edge Resort & Spa

13. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (681 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is CA $307
CA $350 total
includes taxes & fees
Nov 2 - Nov 3
Sag Harbor Inn

14. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (319 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is CA $447
CA $562 total
includes taxes & fees
Nov 18 - Nov 19
Faraway Sag Harbor

15. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (16 reviews)
"The place is lovely. We loved the garden the house the host th alpacas and the beach parking pass. It is really expensive to stay in that area but the place is great"
United States
Bent
The Farmhouse Bed and Breakfast

16. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (300 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is CA $296
CA $373 total
includes taxes & fees
Oct 29 - Oct 30
Oyster Estate

17. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is CA $351
CA $457 total
includes taxes & fees
Nov 2 - Nov 3
American Beech Hotel

18. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
"What a beautiful hotel , clean , quiet , charming . We had a dip in the pool and enjoyed the coffee before we took ferry to sag harbor . The staff was amazing and very helpful throughout our stay. Highly recommended!"
United States
Kate
The price is CA $475
CA $543 total
includes taxes & fees
Oct 31 - Nov 1
Shelter Island House

19. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (46 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
West Neck Guesthouse

20. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1,004 reviews)
"Staff was friendly. Grounds very well kept. But rooms are very dated."
United States
Kevin
The price is CA $114
CA $132 total
includes taxes & fees
Nov 18 - Nov 19
Pier Blue Inn Old Saybrook - Essex
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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.

A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Top Southold Hotel Reviews

More cheap stays in Southold

Hotels in Southold with star rating

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 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 $124 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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