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Top 10 Southold hotels and places to stay

Spark by Hilton Guilford

2.5 star property
8.4 out of 10, Very good, (27)
"Good clean property with great staff "
The price is £122
includes taxes & fees
21 Sept - 22 Sept
Spark by Hilton Guilford

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (335)
"Return visitor. Great stay."
The price is £161
includes taxes & fees
21 Sept - 22 Sept
The Bentley Hotel Southampton

Shorewood Inn

2.5 star property
8.4 out of 10, Very good, (681)
"Good place to stay"
Shorewood Inn

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (204)
"We had a wonderful stay."
The price is £229
includes taxes & fees
16 Sept - 17 Sept
The Shoals Suites and Slips

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1000)
"Good budget friendly hotel"
The price is £65
includes taxes & fees
14 Sept - 15 Sept
Pier Blue Inn Old Saybrook - Essex

Wainscott Woods Retreat

2.0 star property
8.0 out of 10, Very good, (2)
"HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has...
The price is £227
includes taxes & fees
15 Sept - 16 Sept
Wainscott Woods Retreat

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1001)
"Excellent Stay"
The price is £83
includes taxes & fees
21 Sept - 22 Sept
Quality Inn Old Saybrook - Westbrook

Liberty Inn

2.0 star property
7.4 out of 10, Good, (624)
"Service at front desk was very good!"
The price is £65
includes taxes & fees
18 Sept - 19 Sept
Liberty Inn

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (271)
"Great stay. Fantastic location. Wonderful motel providing everything you need. Clean, comfortable and excellent value."
The price is £66
includes taxes & fees
14 Sept - 15 Sept
Clinton Motel

Hampton Bays Hotel on Main

2.0 star property
7.0 out of 10, Good, (57)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
Hampton Bays Hotel on Main

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (308)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
The price is £106
includes taxes & fees
14 Sept - 15 Sept
Hampton's Vacation Inn

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (293)
"Very nice & affordable "
The price is £127
includes taxes & fees
13 Oct - 14 Oct
Windward Shores Ocean Resort

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1007)
"A beautiful resort"
The price is £175
includes taxes & fees
15 Sept - 16 Sept
Water's Edge Resort & Spa

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (448)
" Continental breakfast with sub optimal only waffles nothing else And eight bananas to start"
The price is £64
includes taxes & fees
21 Sept - 22 Sept
Econo Lodge Inn & Suites Old Saybrook Westbrook

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (221)
"Great location, great hotel, great staff! "
Greenporter Hotel

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The price is £349
includes taxes & fees
14 Sept - 15 Sept
The Pridwin Hotel

Hamlet Inn

2.0 star property
8.4 out of 10, Very good, (421)
"Positive: cozy and office staff extremely helpful Negative: Bathrooms outdated with rusty fixtures Missing outlet plate covers Needs dehumidifier, high humidity in room"
The price is £145
includes taxes & fees
14 Sept - 15 Sept
Hamlet Inn

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

2.5 star property
8.6 out of 10, Excellent, (1001)
"I enjoyed every minute of my stay .I felt safe the entire time ."
The price is £151
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (191)
"Nice place to stay out on the east end"
Ocean Vista Resort

The Hampton Maid

2.5 star property
9.0 out of 10, Wonderful, (655)
"Great restaurant and beautiful beaches near by"
The price is £220
includes taxes & fees
15 Sept - 16 Sept
The Hampton Maid
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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.

Top Southold Hotel Reviews

More cheap stays in Southold

More cheap stays in Southold

Find out more about Southold

Find out more about Southold

Top reasons to visit Southold

  • Stunning Beaches: Southold boasts beautiful beaches, perfect for sunbathing, swimming, and enjoying breathtaking sunsets.
  • Charming Vineyards: Explore picturesque vineyards offering wine tasting and scenic views, ideal for a romantic outing.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking to skiing in winter, catering to adventure enthusiasts.
  • Rich Local History: Visit the intriguing Southold Historical Museum to learn about the area's captivating past.
  • Welcoming Accommodations: Choose from charming bed and breakfasts to agritourism stays for a delightful lodging experience.

Find great hotels near Southold

Southold offers a delightful selection of accommodation options, ranging from charming agritourism properties to inviting bed and breakfasts. Whether you're seeking a pet-friendly retreat, a family-friendly getaway, or an adventure-filled experience, you'll discover a variety of hotels to suit your preferences. Explore the beautiful surroundings and find the perfect base for your vacation, with options including the Southold Beach Motel and other top-rated establishments in the area.

  • Sound View Greenport: Nestled just 1.9km from Southold, Sound View Greenport is a charming 3.5-star hotel that captures the essence of a beach getaway. Ideal for beach lovers and pet owners alike, this property offers direct access to the sandy shores. Business travellers will appreciate the thoughtful amenities, including a Meeting Room and Conference Space, making it suitable for both leisure and work. With a pet-friendly policy allowing dogs and cats, guests can enjoy their stay with their furry companions while taking advantage of the delightful seaside atmosphere.
  • The Harbor Front Inn: Located 2.5km from Southold, The Harbor Front Inn is a delightful 3.5-star establishment perfect for business-minded travellers seeking a pet-friendly experience. With a focus on comfort and convenience, this hotel provides essential business amenities while ensuring a welcoming atmosphere for pets. The property allows dogs in guest rooms and has a fee-waived policy for service animals, making it an excellent choice for those travelling with their four-legged friends. The picturesque harbour views add an extra touch to this inviting retreat.
  • Sag Harbor Inn: Situated 5.0km from Southold, Sag Harbor Inn is a sophisticated 3.5-star hotel designed with business travellers in mind. With its essential Meeting Room facilities, this inn caters to those looking to blend work with leisure. The property’s serene environment makes it a perfect escape for professionals who wish to unwind after a busy day. While primarily business-focused, the inn’s charming surroundings and proximity to local attractions ensure a pleasant stay for all guests.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures, romantic settings, and family-friendly activities. Explore the stunning beaches, picturesque vineyards, and charming neighbourhoods that surround this quaint town. From scenic excursions to luxurious experiences, Southold is perfect for those seeking both relaxation and exploration. Don't miss the chance to soak up the sunny weather and rich historical atmosphere during your stay in this beautiful corner of the United States.

  • Hamptons: Located approximately 6.2km from Southold, the Hamptons are famed for their picturesque beaches and vibrant outdoor activities. This idyllic coastal region attracts travellers seeking a romantic getaway or a family holiday, particularly in peak months from May to August. Visitors can enjoy a variety of experiences, including world-class golf courses, lively music concerts, and luxurious resorts. Notable landmarks such as pristine beaches and scenic lakes provide a stunning backdrop for relaxation and exploration.
  • Greenport: Just 2.5km from Southold, Greenport is a charming city that draws visitors with its delightful outdoor spaces and romantic seaside atmosphere. The peak season runs from June to August, when tourists flock to enjoy the local beaches and outdoor events. Greenport offers an array of attractions, including golf courses and music venues, ensuring there's always something to do. With its picturesque family beaches and event conference venues, Greenport makes for a perfect day trip or weekend retreat.
  • Sag Harbor: Situated about 5.0km from Southold, Sag Harbor is a unique city rich in history and coastal beauty. Popular for its outdoor activities and romantic seaside charm, Sag Harbor sees the highest number of visitors from June to August. The area features well-maintained beaches, inviting parks, and opportunities for skiing in winter, catering to a variety of interests. Explore the local golf courses and enjoy the stunning coastal views, making Sag Harbor a delightful addition to your itinerary.

Things to do near Southold

Southold offers a delightful mix of outdoor adventures and romantic experiences, making it ideal for a memorable holiday. Visitors can explore its scenic recreational areas, enjoy skiing during the winter months, and attend vibrant music concerts throughout the year. With its charming atmosphere, Southold is perfect for those seeking entertainment and relaxation in a picturesque setting.

Shopping

For a delightful shopping experience in Southold, visit the Greenport Farmers' Market, just 2.5km away, offering local produce and unique crafts. If you're up for a drive, Victoria's Secret, located 6.8km away, provides stylish lingerie, while Clinton Plaza Shopping Center, 9.3km away, offers a variety of shops and entertainment.

Recreation

Experience fun at Shelter Island Whale's Tail miniGolf, where family-friendly vibes meet sporty adventure, just 3.1km from Southold. For relaxation, visit Goldsmith's Inlet Park, located 1.9km away, offering a serene environment for wellness. Enjoy outdoor sports at Noyac Golf Club, 3.7km from Southold.

Adventure

Splish Splash Water Park, located 11.8km from Southold, offers thrilling water slides and family-friendly attractions for endless fun. For adrenaline seekers, the Long Island Skydiving Center, situated 14.9km away, provides exhilarating jumps with stunning views. Meanwhile, Riverhead Raceway, 11.2km from Southold, promises heart-pounding motor racing excitement.

Nightlife

Experience the charming nightlife of Southold by visiting the Greenport Carousel, a delightful outdoor attraction just 2.5km away, perfect for families. For a touch of culture and romance, the Bay Street Theatre, located 5.0km away, offers captivating performances. Don’t miss the Regal UA Hampton Bays cinema, 12.5km distant, for an entertaining movie night.

Booking tips and Expedia advantages for Southold

To save money on your visit to Southold, consider travelling between January and March, when accommodation prices are lower, particularly on Tuesdays. Avoid weekends, especially Saturdays, for better rates. Use Expedia to filter for budget-friendly options, including eco-certified hotels, and consider bundling your hotel, flights, and activities for extra savings. Explore free local attractions to enhance your experience without added costs. Being strategic about your travel dates and utilising online tools can significantly reduce your expenses during your holiday.

  • 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 budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To discover the best prices and offers, 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 delightful blend of outdoor, romantic, and entertainment options for visitors. Explore its stunning beaches, charming urban parks, and the intriguing Southold Historical Museum. With a variety of attractions catering to those interested in culture and outdoor experiences, Southold is perfect for travellers seeking both relaxation and adventure. Don't miss the chance to discover popular local attractions that showcase the area's rich history and natural beauty.

  • Gardiner's Bay Country Club: Experience a round of golf at this picturesque course, located 3.1km from Southold. Enjoy stunning views of Gardiner's Bay while navigating its beautifully designed fairways, perfect for both seasoned players and beginners.
  • Orient Point County Park: This urban park, situated 7.5km away, offers a family-friendly atmosphere with outdoor activities. Enjoy picnicking, hiking, and stunning views of the water, making it an ideal spot for relaxation and fun.
  • Orient Beach State Park: Located 5.6km from Southold, this beach provides a quintessential seaside experience. Soak up the sun, swim in the ocean, or stroll along the shore, enveloped in the soothing beach vibes.

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.

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 HighAverage
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 SunnyAverageSlightly High
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

If you're planning a visit to Southold, New York, there are several airports to consider. Islip Airport (ISP-MacArthur) is situated 24.9km away, with nearby hotels such as the 3.5-star Hyatt Regency Long Island and Jake's 58 Casino Hotel, both 2.5km from the airport. Westhampton Airport (FOK-Francis S. Gabreski) is 11.8km from Southold, offering options like the 4-star Canoe Place Inn and Cottages. Lastly, New Haven Airport (HVN-Tweed) is 17.4km away, with fine accommodations including the 4-star Omni New Haven Hotel at Yale. Each airport provides convenient access to local hotels for a comfortable stay.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What are the best hotels in Southold that travellers recommend?
The Shoals Suites and Slips is a highly praised destination in Southold, boasting an impressive traveller review score of 9.4. This charming hotel is great for couples seeking a romantic getaway, offering premium bedding, luxurious bathrobes, and attentive champagne service that sets the mood for an intimate experience. Guests love the opportunity to explore nearby vineyards with private tours and tastings, making it a delightful choice for wine enthusiasts looking to unwind in a serene setting.

For families, Vine & Sand stands out with a great review score of 10.0. This hotel promises comfort and convenience, featuring premium bedding and designer toiletries that ensure a restful stay. Families will appreciate the spacious rooms and the opportunity to enjoy the beautiful vineyard views right from their doorstep. With rainfall showerheads and a inviting space, it's an inviting spot for relaxation after a day of exploring local attractions.
What are the best family hotels in Southold?
The Shoals Suites and Slips in Southold stands out as an exceptional family-friendly hotel, boasting a stellar review score of 9.4 from guests who appreciate its attentive service and comfortable accommodations. This charming property offers a range of amenities designed to cater to families, including complimentary cribs and a daily housekeeping service, ensuring that parents can enjoy a stress-free stay while their little ones are well taken care of. Find more child-friendly accommodations in Southold.
What hotels in Southold offer free breakfast?
Vine & Sand in Southold is an exceptional choice for travellers seeking a serene retreat complemented by attentive service. With a superb customer review rating of 10.0, this hotel stands out not only for its picturesque vineyard views but also for its delightful amenities. Find more hotels with free breakfast in Southold.
What are the top pet-friendly hotels in Southold?
The Shoals Suites and Slips in Southold, NY, is a charming pet-friendly hotel that welcomes furry companions while offering an exceptional stay for their owners. This beautifully situated property boasts a stunning white sand beach, great for morning strolls with your pet. Guests rave about the attentive service and thoughtful amenities, including premium bedding, air conditioning, and a kitchenette, ensuring a comfortable and convenient experience. See more pet-friendly hotels in Southold.
What are the best budget hotels in Southold?
For travellers seeking charming accommodations in Southold, Vine & Sand is an exceptional option, boasting a great review score of 10.0. This hotel offers a delightful array of amenities, including free Wi-Fi and complimentary breakfast on weekends, ensuring a comfortable stay without breaking the bank. Guests can enjoy the seasonal outdoor pool, relax on the terrace, or take in the beautiful vineyard views. The nearby private beach with sun loungers and umbrellas provides an ideal spot for families to unwind.

Another top property is The Shoals Suites and Slips, which has received high praise with a traveller review score of 9.4. This hotel features a kitchenette in each suite, great for families who prefer the convenience of preparing their own meals. The property also offers access to a stunning white sand beach and organizes public tours and tastings at their on-site winery, making it a fantastic choice for couples looking for a romantic getaway while still appealing to families. View all budget hotels in Southold.
What are the most romantic hotels in Southold for couples?
For couples seeking a romantic escape, The Shoals Suites and Slips in Southold is an exceptional choice, boasting an impressive customer review rating of 9.4. This hotel features an array of amenities designed to enhance your romantic getaway, including couples dining options that set the stage for intimate meals together. See all romantic hotels in Southold.
When is the best time to go to Southold?
The most popular time to visit Southold is during the summer months, particularly July, when the weather is warm and inviting. With average temperatures ranging from 22 to 27°C, this is the superb season for enjoying the beautiful beaches, exploring local wineries, and taking part in outdoor activities.

During the peak season, which runs from June to August, Southold comes alive with vibrant tourist activity. Visitors flock to the area for its stunning coastal views and charming small-town atmosphere. This time of year is especially enjoyable for those who appreciate leisurely days spent cycling through scenic vineyards or indulging in fresh seafood at waterfront restaurants, where you can savour the local cuisine while soaking in the sun.

For families and couples alike, July offers numerous festivals and events that showcase the best of Southold's culture and community spirit. Whether it's a local art fair or a concert in the park, there's always something happening to enhance your visit. The long days and pleasant evenings provide ample time to explore and relax.

If you're looking for a slightly quieter experience, consider planning your trip in September. The weather remains pleasant, with temperatures still hovering around 20 to 24°C, and you'll find that prices for accommodations and activities often drop as the summer crowds disperse. This is a wonderful opportunity to enjoy the area's natural beauty without the hustle and bustle of peak season.
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?
Before booking your Southold hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.
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 £64 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.