"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."
"The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing."
"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."
"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."
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.
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.
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.
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.
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.
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.
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.
Long Island's oldest public observatory invites you to explore the cosmos through powerful telescopes every Saturday night. Enjoy guided stargazing at this historic astronomical sanctuary established in 1927.
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.
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.
The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing.
The shoals was a perfect place for our north fork adventures. The staff was very friendly and extremely accommodating! The location was beautiful and very relaxing.
William
Reviewed November 12, 2026Reviewed November 12, 2026
Quick anniversary night get away! Location was great, rooftop was amazing, and staff was super helpful! Made our stay special and memorable! Cant wait to go back for 2 nights!! Or more!
Quick anniversary night get away! Location was great, rooftop was amazing, and staff was super helpful! Made our stay special and memorable! Cant wait to go back for 2 nights!! Or more!
Anonymous traveler
Reviewed September 8, 2021Reviewed September 8, 2021
My stay was perfect. This family run hotel is outstanding, and great value for the money. Room (facing pool) was large, quiet and in perfect condition. Small private terrace with lounge chairs a big plus. Bathroom is large and modern with 5 star amenities (I appreciate that). Entire hotel feels like it was recently renovated. Will definitely stay here again!
My stay was perfect. This family run hotel is outstanding, and great value for the money. Room (facing pool) was large, quiet and in perfect condition. Small private terrace with lounge chairs a big plus. Bathroom is large and modern with 5 star amenities (I appreciate that). Entire hotel feels like it was recently renovated. Will definitely stay here again!
It’s a nice hotel, it has a funky vibe to it and it’s very clean and the rooms are excellent. I definitely recommend it’s the perfect couple gate away hotel. Definitely coming back!!
It’s a nice hotel, it has a funky vibe to it and it’s very clean and the rooms are excellent. I definitely recommend it’s the perfect couple gate away hotel. Definitely coming back!!
everything was excellent. The only comment I would have is that the hallways smelled funny. Maybe if they could put a more fresh aroma and that’ll be great. Staff, everything was awesome.
everything was excellent. The only comment I would have is that the hallways smelled funny. Maybe if they could put a more fresh aroma and that’ll be great. Staff, everything was awesome.
Maureen
Reviewed October 22, 2023Reviewed October 22, 2023
Beautiful view and excellent location. A short walk to the ferry to Greenport and a short drive to preserves. Owner more than accommodating. I will visit again.
Beautiful view and excellent location. A short walk to the ferry to Greenport and a short drive to preserves. Owner more than accommodating. I will visit again.
Our stay was amazing! We had the best beach view! It was relaxing and one of the best getaways we’ve been on. If you want to connect to Netflix, HBO max, etc… bring a laptop or a console like Xbox, etc, bring a usb cord and wala you could connect. Thank you! We will be back!
Our stay was amazing! We had the best beach view! It was relaxing and one of the best getaways we’ve been on. If you want to connect to Netflix, HBO max, etc… bring a laptop or a console like Xbox, etc, bring a usb cord and wala you could connect. Thank you! We will be back!
Marilyn
Reviewed October 15, 2021Reviewed October 15, 2021
We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got.
We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and drinks were amazing. We wanted peace and tranquility and that’s exactly what we got.
Joseph
Reviewed November 8, 2026Reviewed November 8, 2026
We really enjoyed the room and the location. Our only criticism is that we were not able to access our room until 5:00 and we had to check out by 10 am in the morning. We basically lost at least half a day.
We really enjoyed the room and the location. Our only criticism is that we were not able to access our room until 5:00 and we had to check out by 10 am in the morning. We basically lost at least half a day.
The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests.
The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests.
Very nice romantic getaway for two. Took in the local sites, beaches and shops. The Inn was lovely. Very pleasant staff and guests. Would certainly recommend and would stay here again and again!
Very nice romantic getaway for two. Took in the local sites, beaches and shops. The Inn was lovely. Very pleasant staff and guests. Would certainly recommend and would stay here again and again!
Scenic Wine Tastings: Southold is renowned for its picturesque vineyards, offering delightful wine tastings amid beautiful landscapes.
Beautiful Beaches: Enjoy sun-soaked relaxation on Southold's stunning beaches, perfect for unwinding and soaking in the sun.
Outdoor Adventures: Explore various outdoor activities, from hiking in parks to family-friendly excursions suitable for all ages.
Rich Historical Experiences: Discover local history at nearby museums and charming towns, enhancing your cultural journey.
Diverse Accommodations: Find unique lodging options, from cozy beach motels to family-oriented hotels catering to various needs.
Find great hotels near Southold
Discover a variety of hotel accommodations in Southold, New York, perfect for your vacation needs. From pet-friendly options to family-oriented experiences, Southold offers unique agritourism properties and comfortable hotels. Whether you're seeking a charming beach motel or a cozy retreat, you'll find options that cater to adventure seekers and relaxation lovers alike. Read reviews to help you choose the ideal place for your memorable getaway.
Sound View Greenport: Nestled along the picturesque coastline, Sound View Greenport is a family-friendly hotel that offers a delightful beach vacation experience just 4.8km from Southold. This 3.5-star property features direct access to the beach, allowing guests to enjoy the sun and surf with ease. Families will appreciate the thoughtful amenities for children, including complimentary cribs and window guards for safety. The hotel’s serene atmosphere and stunning waterfront views make it an ideal retreat for both relaxation and adventure.
The Harbor Front Inn: Located 6.4km from Southold, The Harbor Front Inn is a charming, pet-friendly hotel perfect for travelers seeking a blend of business and leisure. Rated at 3.5 stars, this inn welcomes pets with open arms, making it an excellent choice for those who want to bring their furry companions along. With amenities catering to pets, including in-room accommodations and a waived fee for service animals, guests can enjoy a stress-free stay. The hotel’s waterfront location offers beautiful views and a relaxing atmosphere.
Sag Harbor Inn: Situated 12.9km from Southold, the Sag Harbor Inn is a sophisticated choice for business travelers. This 3.5-star hotel combines comfort and convenience, making it an ideal base for those attending meetings or events in the area. The inn features well-appointed rooms and modern amenities that cater to the needs of business guests. Its location in the charming village of Sag Harbor allows visitors to explore local shops and dining options after a productive day.
Where to stay near Southold
Southold, nestled in New York's North Fork on Long Island, offers a perfect blend of outdoor adventures and romantic getaways. Enjoy family-friendly activities, from exploring scenic vineyards to relaxing on sunny beaches. Nearby towns provide rich historical experiences and luxury excursions, making it an ideal destination for travelers seeking both tranquility and entertainment. Discover the charm of Southold and its surrounding areas for an unforgettable vacation experience.
Hamptons: Located 16.1km from Southold, the Hamptons are a renowned vacation destination celebrated for their beautiful beaches and vibrant outdoor activities. With traveler numbers peaking from June to August, this area attracts visitors seeking a romantic seaside getaway. Popular activities include golf at local courses, enjoying music concerts, and lounging at family-friendly beaches. Key landmarks include pristine beaches and scenic lakes, making it an ideal spot for relaxation and recreation.
Greenport: Just 6.4km from Southold, Greenport is a charming city that offers a delightful blend of outdoor adventures and romantic escapes. With similar seasonal travel patterns, visitors flock here in the summer months. Greenport features a variety of activities such as golfing, attending local music concerts, and exploring recreational areas. Notable attractions include beautiful beaches and parks, providing ample opportunities for leisurely strolls and picnics by the water.
Sag Harbor: Situated 12.9km from Southold, Sag Harbor is a picturesque city that captures the essence of coastal living. Like its neighboring areas, it sees peak travel during the summer, drawing tourists looking for outdoor and beach experiences. Visitors can enjoy golfing, skiing, and exploring local beaches, including family-friendly options. The iconic lighthouse stands as a local landmark, offering stunning views and a glimpse into the area's maritime history.
Things to do near Southold
Southold offers a delightful mix of outdoor and romantic activities perfect for your vacation. Enjoy scenic wine tastings at local vineyards, indulge in skiing at nearby resorts, and explore the beautiful landscapes. With its charming ambiance and entertainment options, Southold is an ideal destination for a memorable getaway.
Shopping
The Greenport Farmers' Market, located 6.4km away, offers a vibrant local atmosphere with fresh produce and unique crafts. The Style Bar and Love Lane, both 12.9km away, provide a charming shopping experience with a mix of family-friendly stores and boutiques. If you're up for a drive, check out additional nearby shopping options.
Recreation
Goldsmith's Inlet Park offers a tranquil retreat with scenic views and serene walking paths, perfect for relaxation. At Noyac Golf Club, enjoy a round of golf amidst beautiful landscapes that promote outdoor recreation. Shelter Island Whale's Tail mini-golf provides family-friendly fun and adventure for all ages.
Adventure
Experience the thrills at Splish Splash Water Park, located 30.6km from Southold, featuring exciting water slides and family attractions. For adrenaline seekers, Riverhead Raceway, 29.0km away, offers exhilarating motor racing. Enjoy nature at the Walking Dunes Trailhead, 33.8km distant, with stunning scenery and outdoor adventures.
Nightlife
In Southold, the Greenport Carousel offers charming outdoor vibes just 6.4km away, perfect for a whimsical evening. For a touch of romance and culture, head to Bay Street Theatre, 12.9km away, or Guild Hall, located 16.4km away, both showcasing captivating performances.
*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 during the low season from January to March when prices drop. Tuesday is the most economical day for accommodations, while Saturdays tend to be pricier. Use Expedia to compare room rates and find eco-certified hotels for better savings. Look for package deals that combine flights and activities with your hotel stay for additional discounts. Explore free local attractions and utilize public transport options to minimize travel costs while enjoying 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: Utilize Expedia's search tool to refine your preferences, such as budget, desired location, and the type of hotel you’re looking for. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply 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 through an Expedia package.
Find the best attractions near Southold
Southold offers a charming blend of outdoor adventures and romantic escapes, making it ideal for a memorable vacation. Visitors can enjoy beautiful beaches, explore urban parks, and delve into local history at nearby museums. Whether you're looking for sun-soaked relaxation or cultural experiences, Southold's attractions cater to all, ensuring a delightful getaway filled with nature and enriching activities.
67 Steps Beach: Experience the serene beach vibes at 67 Steps Beach, located 8.0km from Southold. This picturesque spot features a unique staircase leading down to soft sands, perfect for soaking up the sun or enjoying a leisurely stroll along the shore.
Railroad Museum of Long Island: Immerse yourself in local culture at the Railroad Museum of Long Island, just 6.4km away. This fascinating museum showcases the rich history of railroads in the region, featuring vintage trains and informative exhibits that are sure to delight history enthusiasts.
Sag Harbor Marine Park: For outdoor adventure, visit Sag Harbor Marine Park, situated 12.9km from Southold. This marina offers various activities like kayaking and fishing, along with stunning views and a relaxing beach atmosphere perfect for family outings.
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 Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
35.6°F (2.0°C)
Light Rain
Mostly Sunny
Moderately Low
Slightly Low
February
35.8°F (2.1°C)
Light Rain
Mostly Cloudy
Average
Slightly Low
March
39.7°F (4.3°C)
Light Rain
Mostly Sunny
Average
Slightly Low
April
47.5°F (8.6°C)
Light Rain
Mostly Sunny
Average
Average
May
55.8°F (13.2°C)
Light Rain
Mostly Sunny
Average
Average
June
64.9°F (18.3°C)
Light Rain
Mostly Sunny
Moderately High
Slightly High
July
73.0°F (22.8°C)
Light Rain
Mostly Sunny
Moderately High
Slightly High
August
73.4°F (23.0°C)
Light Rain
Mostly Sunny
Moderately High
Slightly High
September
68.2°F (20.1°C)
Light Rain
Mostly Sunny
Average
Average
October
59.7°F (15.4°C)
Light Rain
Mostly Sunny
Average
Average
November
49.6°F (9.8°C)
Light Rain
Mostly Sunny
Moderately Low
Average
December
42.1°F (5.6°C)
Light Rain
Mostly Cloudy
Moderately Low
Average
The nearest major airports for your trip to Southold
When planning your trip to Southold, New York, you can choose from several nearby airports. Islip, NY (ISP-MacArthur) is 64.4km away and offers hotels like Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 6.4km from the airport. New Haven, CT (HVN-Tweed) is another option, situated 45.1km away, with top-rated hotels such as Omni New Haven Hotel at Yale, just 4.8km from the airport. Lastly, East Hampton, NY (HTO) is conveniently located 19.3km away, with luxury accommodations like Mill House Inn and Topping Rose House, both within 4.8km of the airport, making travel to Southold easy and comfortable.
Frequently Asked Questions
What's the top vacation rental in Southold?
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental outside of Southold offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. 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?
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?
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.
To see more of the larger area, hop aboard a train at Southold Station.
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.