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Southold holiday lettings

We found 977 holiday rentals — enter your dates for availability

Select from 120 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:15 May - 22 May

Image gallery for Renovated Farmhouse on Vineyard w/ Heated Pool, mins from Beach + Farm

Heated outdoor pool with lounge chairs, plus sitting area w/ sofa and chairs
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Renovated Farmhouse on Vineyard w/ Heated Pool, mins from Beach + Farm

Riverhead

8% off
Price is £4,733
for 7 nights, 1 room
£676 per night
includes taxes & fees
Renovated Farmhouse on Vineyard w/ Heated Pool, mins from Beach + Farm

Find spaces that suit your style

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)
  • Macari Vineyards (9.2 mi / 14.7 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:

  • 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)
  • LongHouse Reserve (13.1 mi / 21.1 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, the area known for its charm and picturesque scenery is the North Fork. This region boasts a delightful selection of properties, often reflecting the maritime heritage of the area. You can typically find a mix of quaint cottages and spacious family homes, providing a comfortable base for your stay.

One of the top attractions in North Fork is the stunning array of vineyards and wineries, where you can indulge in tastings and enjoy the beautiful countryside views. Additionally, the nearby beaches, such as those at the Orient Beach State Park, offer lovely spots for relaxation and recreation. The local seafood restaurants are also a highlight, serving fresh catches that reflect the area's coastal culture.
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, the area along the North Fork of Long Island is particularly appealing. The stretch near Southold Bay offers picturesque views and direct access to the sandy shores, making it a great spot for beach enthusiasts. Many properties in this area feature amenities such as spacious outdoor decks, private gardens, and beach access, ideal for families or groups looking to enjoy the coastal lifestyle.

Additionally, the nearby Hashamomuck Pond area provides options for those who prefer a more tranquil setting. Rentals here often come equipped with modern kitchens, barbecue grills, and relaxing lounge areas, allowing visitors to enjoy al fresco dining while soaking in the serene surroundings. This part of Southold is also known for its proximity to local vineyards and farm stands, which enhance the overall experience for travellers seeking a taste of the region's charm.

For a more vibrant setting, exploring the beach houses closer to the town centre can be rewarding. These properties are typically within walking distance of cafes, shops, and recreational activities. Many of them come with communal amenities like swimming pools or private access to beach clubs, ensuring a lively holiday experience.
What is the most popular type of holiday rental accomodation in Southold?
In Southold, holiday houses are the predominant type of holiday rental, with approximately 372 available across this charming coastal town. These properties are often situated in scenic locations, providing easy access to local beaches and vineyards. Most holiday houses come equipped with multiple bedrooms, spacious living areas, and fully stocked kitchens, ideal for families or groups looking to enjoy a home-like experience. Additionally, about 48 cottages offer a quaint alternative, featuring cosy interiors and sometimes outdoor spaces for relaxation. For those seeking a more compact option, there are around 12 apartments, typically located within walking distance of local attractions and eateries.
Are there any family house rentals in Southold?
In Southold, New York, there are around 80 family-friendly holiday rentals available, making it an excellent choice for those travelling with children. This charming town, located on the North Fork of Long Island, offers a variety of accommodations that cater to families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and adults can relax.

Visitors can explore nearby attractions such as the beautiful beaches along the Long Island Sound, ideal for swimming and picnicking. The local vineyards present opportunities for tours and tastings, providing a great experience for the whole family. Additionally, the town's proximity to nature reserves and parks ensures plenty of outdoor activities, from hiking to birdwatching.
Can I rent a holiday home with a pool or hot tub in Southold?
In Southold, there are a variety of holiday homes available for rent that feature pools and hot tubs, with around 32 options to choose from. This charming town on Long Island's North Fork is known for its beautiful vineyards, scenic waterfronts, and quaint atmosphere.

Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens great for family meals. Many properties also offer features such as outdoor patios, barbecue grills, and beautiful gardens, providing an ideal setting for a tranquil getaway.
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, providing a welcoming environment for travellers with furry companions. Many of these holiday homes come equipped with essential amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces that are superb for pets to roam and play. Some properties may also feature private gardens or patios, allowing for a relaxed atmosphere after a day of exploring the area.

The town is known for its picturesque landscapes and proximity to the waterfront, which makes it an attractive destination for those looking to enjoy nature with their pets. Nearby beaches and parks offer plenty of opportunities for walks and outdoor activities.
Are there any remote work holiday rentals in Southold?
In Southold, New York, there is a substantial selection of remote work holiday rentals available, with around 392 options to choose from. This picturesque town on Long Island's North Fork offers a serene environment ideal for working remotely while enjoying the beauty of coastal living. Many properties feature essential amenities such as high-speed internet and Wi-Fi, ensuring that guests can stay connected during their stay.

Accommodations often include dedicated workspaces or desks, which provide a comfortable setting for productivity. Additionally, some rentals boast outdoor spaces, allowing for a refreshing break during work hours. Southold is also known for its charming local attractions, including vineyards and beaches, making it a great blend of work and leisure. 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 holiday rental amenities include well-equipped kitchens, allowing travellers to prepare their own meals with ease. Many properties also feature decks or patios, superb for enjoying the serene surroundings and fresh air. A fireplace is common in these rentals, providing a cosy atmosphere during cooler evenings. Additionally, amenities such as a blender are available for those who enjoy making smoothies or other blended drinks. Onsite parking is also a convenient feature offered by many rentals, making it easier for guests to explore the beautiful North Fork region of Long Island.
When is the best time to visit Southold for a holiday rental?
The peak season for visiting Southold typically runs from June to August, with July being the most popular month for holiday rentals. During this vibrant period, the charming coastal town comes alive with summer activities. Visitors can soak up the sun on beautiful beaches, explore local vineyards, and enjoy various outdoor festivals that showcase the best of Long Island's summer spirit.

The pleasant summer climate, with temperatures averaging around 20 to 30 degrees Celsius, makes it an ideal time for outdoor adventures and leisurely strolls along the picturesque shoreline. Whether you're interested in wine tasting, cycling through scenic routes, or simply basking in the sun, Southold offers an abundance of enjoyable experiences.

For those looking for a more budget-friendly option, consider visiting in December. While this month may be quieter, Southold still has its unique charm, with the opportunity to enjoy peaceful walks along the beach and cosy evenings by the fire in your holiday rental.

Ultimately, your choice of when to visit Southold will depend on whether you prefer the lively option of summer or the tranquil beauty of the off-season.
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 explore a variety of attractions that showcase the charm of this picturesque town. The Southold Historical Society offers insights into the local history, featuring exhibits and preserved buildings that reflect the area's maritime heritage. Nearby, the beautiful beaches along the Long Island Sound, such as Founders Landing Park, provide opportunities for swimming, picnicking, and enjoying stunning sunsets.

Wine enthusiasts will appreciate the proximity to the North Fork's vineyards, with several wineries offering tastings and tours just a short drive away. The scenic landscapes of these vineyards create a lovely backdrop for leisurely afternoons. For nature lovers, the Southold Town Park at Cedar Beach is a great spot for walking trails and birdwatching, while the nearby Orient Beach State Park features sandy shores and scenic views of the water.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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