Southold holiday lettings

We found 1,001 holiday rentals — enter your dates for availability

Select from 125 homes, 13 cottages and other holiday rentals in Southold to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Southold

Showing deals for:14 Nov - 21 Nov

Image gallery for Peconic River Boatel

Outdoor dining
10 out of 10 rating
Exceptional
(18 reviews)

Peconic River Boatel

Riverhead, NY

8% off
Price is £2,663
£380 per night
includes taxes & fees
Peconic River Boatel

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Find out more about Southold

Find out more about Southold

Why visit Southold

  • Beautiful beaches: Southold boasts stunning sandy shores, perfect for sunbathing and relaxation.
  • Historic charm: Wander through quaint streets lined with historic houses, immersing yourself in local heritage.
  • Outdoor activities: Enjoy a range of outdoor pursuits, from hiking in tranquil parks to family-friendly excursions.
  • Scenic neighbourhoods: Explore picturesque areas offering scenic views and luxury experiences.
  • Comfortable accommodations: Choose from charming cottages to modern apartments, catering to every traveller's needs.

Popular types of accommodation in Southold

Discover a variety of vacation rentals in Southold, perfect for your getaway. Whether you’re seeking a charming cottage, a spacious private home, or a modern apartment, we have something to suit every traveller. Popular options include holiday homes, condos, and townhouse rentals, ensuring a comfortable stay tailored to your needs. Explore Southold and create lasting memories with the ideal accommodation choice for your trip.

  • Houses: The top choice for visitors in Southold, these homes offer spacious and comfortable accommodations perfect for families or groups.
  • Cottages: A charming option, cottages provide a quaint and cosy atmosphere, ideal for a peaceful getaway.
  • Apartments: Popular among solo travellers and couples, apartments offer convenience and flexibility during your stay.
  • Condos: These modern dwellings combine luxury with practicality, making them a sought-after option for vacationers.
  • Villas: For those seeking elegance, villas offer upscale living with ample space and amenities.**

Top attractions near Southold

Southold offers a delightful blend of outdoor activities, romantic spots, and vibrant entertainment options, making it an ideal vacation destination. Visitors can explore beautiful beaches, tranquil urban parks, and fascinating museums that reflect the area's rich history. Whether you're seeking a cultural experience or simply wish to enjoy the great outdoors, Southold has something to cater to every traveller's preference.

  • 67 Steps Beach: A beautiful sandy beach offering a relaxing atmosphere, 67 Steps Beach is perfect for sunbathing and swimming. Enjoy the soothing sounds of the waves as you unwind in this picturesque coastal setting, located 3.1km from Southold.
  • Railroad Museum of Long Island: Immerse yourself in local culture at this fascinating railway museum, showcasing historical trains and exhibits. Just 2.5km from Southold, it's a delightful trip for history buffs and families alike.
  • Sag Harbor Marine Park: Experience adventure at this vibrant marina, 5.0km from Southold, where you can partake in water sports, fishing, and outdoor activities while enjoying stunning views of the waterfront.

Things to do recommended for couples

Planning a romantic getaway in Southold? Delight in wine tasting at Pindar Vineyards or Raphael Winery, both offering enchanting atmospheres. For a touch of adventure, enjoy a round of mini golf at Shelter Island Whale's Tail, perfect for creating cherished memories together.

Things to do recommended for families

Families will love the charming Greenport Carousel, a delightful outdoor attraction just 2.5km from Southold. For relaxation, visit Goldsmith's Inlet Park, 1.9km away. For adventure, the Splish Splash Water Park, located 11.8km from Southold, offers fantastic entertainment for all ages.

Things to do recommended for groups

Explore the Greenport Farmers' Market for a taste of local produce and vibrant community spirit, enjoy a round of golf at Noyac Golf Club amidst beautiful surroundings, and catch a performance at the Bay Street Theatre for a delightful evening of culture and entertainment.

What do I need to keep in mind when booking a vacation in 'Southold

When planning your journey, whether it’s with a group, family, or pets, or if you’re seeking a longer stay, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Southold with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Southold with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Southold: For many families, a holiday isn’t truly enjoyable without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Southold: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic escapades, perfect for a memorable getaway. Explore the charming streets lined with historic houses, enjoy family-friendly excursions, and soak up the sunny weather. Nearby, discover picturesque neighbourhoods boasting scenic views and luxury experiences. Whether you're wandering through Southold Town or seeking the best spots for relaxation, this region is sure to captivate every traveller.

  • Hamptons: Situated approximately 6.2km from Southold, the Hamptons are renowned for their picturesque beaches and upscale atmosphere. This idyllic retreat is a favourite for couples seeking a romantic getaway, as well as families eager to enjoy outdoor activities. Visitors can indulge in a round of golf, attend a lively music concert, or relax at luxurious resorts. Notable nearby attractions include pristine beaches, family-friendly shorelines, and serene lakes, making it a perfect destination for sun-seekers and nature lovers alike.
  • Greenport: Located a mere 2.5km away from Southold, Greenport is a charming town that offers a delightful mix of outdoor experiences and romantic settings. Its scenic waterfront and quaint streets invite exploration, whether you're enjoying a day at the beach or attending a local event at a conference venue. The area is also home to various golf courses and music venues. Greenport’s local landmarks, including family beaches, make it a welcoming spot for visitors looking to unwind and embrace the beauty of coastal living.
  • Sag Harbor: Nestled 5.0km from Southold, Sag Harbor boasts a rich maritime history and a vibrant community atmosphere. This coastal town is celebrated for its outdoor spaces and beautiful beaches, making it an ideal location for romantic strolls or family outings. Visitors can partake in activities such as golfing or skiing, adding an adventurous twist to their stay. Local highlights include family beaches and picturesque parks, offering ample opportunities for relaxation and recreation amidst Sag Harbor's stunning natural surroundings.

Best time to go to Southold

If you're planning a trip to Southold, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately 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 HighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighModerately 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

Booking with Vrbo is simple

Are you hoping to save on your next getaway? It’s worth being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new trips, pick up from where you last stopped, or view and arrange your travel plans. You can conveniently find properties you've previously saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Southold

The area's wineries and monuments are just some of the reasons to come on holiday to Southold. Renowned for its island views, beaches and gardens, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Southold

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southold a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Raphael Winery (2.7 mi / 4.4 km)
  • Pindar Vineyards (3 mi / 4.9 km)
  • Bedell Cellars (3.3 mi / 5.3 km)
  • Peconic Bay Winery (4.2 mi / 6.8 km)
  • Kontokosta Winery (4.7 mi / 7.6 km)
  • Noyac Golf Club (6.5 mi / 10.4 km)

Exploring the natural landscape of Southold

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Southold is a great spot to appreciate mother nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Crescent Beach (2.9 mi / 4.7 km)
  • Sunset Beach (3.2 mi / 5.2 km)
  • 67 Steps Beach (4.8 mi / 7.8 km)
  • The Hamptons Beaches (11.6 mi / 18.6 km)
  • Orient Point County Park (11.7 mi / 18.8 km)
  • Meschutt Beach (12.4 mi / 19.9 km)

Transport to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you prefer train travel, the main station is Southold Station.

Frequently asked questions

What is the best area to stay in Southold when booking a holiday rental?
When considering a holiday rental in Southold, New York, a popular area to stay is along the picturesque North Fork coastline. This region offers a tranquil atmosphere, stunning views of the Long Island Sound, and easy access to local attractions. You'll find a delightful array of properties, from charming cottages to modern homes, suiting various preferences and budgets.

The area near Southold's historic village centre is particularly appealing, as it provides a blend of quaint shops, eateries, and cultural sites. A visit to the Southold Historical Society is a must for those interested in local history, offering insights into the town's rich past. Additionally, you can explore the nearby vineyards, which are famous for their exquisite wines and beautiful vineyard landscapes, great for leisurely strolls or wine tastings.

Another lovely option is to look for rentals close to the beaches, such as those near Horton Point Park. This scenic area not only features a stunning lighthouse but also offers excellent opportunities for hiking and enjoying nature. The serene beaches provide a great backdrop for relaxation and recreation, making it an ideal choice for families or couples seeking a peaceful getaway.
How much does it cost to rent a holiday home in Southold?
Prices for holiday rentals in Southold vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Southold to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Southold holiday house rentals?
You can find great discounts on house rentals in Southold on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Southold?
For renting a beach house in Southold, New York, the area along the North Fork of Long Island is particularly appealing. The beachfront properties near the picturesque Southold Town Beach provide easy access to the sandy shores and stunning views of the Long Island Sound. Many of these homes come equipped with modern amenities such as outdoor decks, barbecue grills, and spacious living areas, great for families or groups looking to enjoy a seaside retreat.

Additionally, the area around Founders Landing Park is a great option, where charming cottages and larger homes often feature private gardens, outdoor seating, and sometimes even direct beach access. This neighbourhood offers a peaceful atmosphere while still being close to local attractions, including boutique shops and wine tasting rooms that showcase the region's renowned vineyards.
What is the most popular type of holiday rental accomodation in Southold?
In Southold, holiday houses are the most popular type of rental, with around 100 available throughout the area. These spacious homes often come with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them ideal for families or larger groups seeking a relaxing getaway. Additionally, there are about 13 cosy cottages scattered along the picturesque coastline, providing a more quaint and intimate atmosphere. While the selection of apartments is limited, they typically feature essential amenities for a comfortable stay.
Are there any family house rentals in Southold?
In Southold, New York, there are numerous family-friendly holiday rentals available—about 86 in total. This charming town, located on the North Fork of Long Island, is known for its beautiful beaches, vineyards, and quaint atmosphere, making it an ideal spot for family getaways.

Many of these homes feature spacious living areas and fully equipped kitchens, superb for preparing meals together after a day of exploring. Outdoor amenities such as gardens or patios provide ample space for children to play, while some properties may also include features like BBQ grills or fire pits for evening gatherings.
Can I rent a holiday home with a pool or hot tub in Southold?
In Southold, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 35 options to choose from. This picturesque town on Long Island's North Fork offers a charming coastal atmosphere, making it an excellent destination for relaxation and leisure. Many of these properties are located near the waterfront, providing easy access to beaches and beautiful views of the Peconic Bay.
Can I find long-stay holiday rentals in Southold?
A long-stay holiday rental in Southold is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Southold?
In Southold, there are numerous pet-friendly house rentals available, making it an excellent destination for travellers looking to enjoy a getaway with their furry companions. The area features a variety of properties, from charming cottages to spacious family homes, many of which come equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and sometimes even private gardens or decks superb for relaxing after a day of exploration.

Southold is well-known for its picturesque landscapes, including vineyards and scenic waterfronts. While enjoying your stay, you can visit nearby parks that are welcoming to pets, such as the beautiful Orient Beach State Park, which offers walking trails and sandy shores where pets are allowed on a leash. Additionally, the local beaches provide opportunities for leisurely strolls with your pet, ensuring that both you and your companion can fully enjoy the natural beauty of the area.
Are there any remote work holiday rentals in Southold?
In Southold, New York, there are numerous remote work-friendly holiday rentals available, with around 103 options to choose from. This charming coastal town offers a serene environment ideal for working remotely while enjoying the beauty of the North Fork. Many properties cater specifically to remote workers, featuring amenities such as Wi-Fi, dedicated desk spaces, ergonomic chairs, and even office setups complete with computer monitors.

Travellers can expect comfortable living spaces that often include fully equipped kitchens, allowing for convenient meal preparation during work breaks. Additionally, some rentals offer outdoor areas where one can relax and unwind after a productive day; these spaces may include patios, gardens, or even scenic views of the surrounding area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Southold holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Southold with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Southold?
In Southold, popular rental amenities include fully equipped kitchens, which are essential for travellers looking to prepare their own meals. Most properties also feature microwaves and dishwashers, adding convenience for guests. Additionally, many holiday rentals come with private patios, providing outdoor spaces to relax and enjoy the pleasant surroundings.
How early should I book a Southold holiday rental?
Book your Southold holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Southold?
In Southold, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque beaches along the North Fork, such as Founders Landing Park, are great for sunbathing and swimming, while the nearby Southold Town Beach offers a more tranquil setting. Holiday rentals in this area often provide easy access to these scenic spots.
Can I change or cancel my Southold home rental booking on Vrbo?
To find Southold holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Southold holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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