Southold holiday lettings

• Peace of mind

  Our Book with Confidence Guarantee gives you 24/7 support

• More quality time

  From booking to staying, the whole process is simple and enjoyable

• All the privacy of home

  Enjoy full kitchens, pools, gardens and more

• More for less

  More space, more privacy, more amenities — more value

Find out more about Southold

Why visit Southold

• Picturesque Beaches: Southold boasts stunning coastal views and serene sandy shores, perfect for relaxation and sunbathing.
• Historic Lighthouses: Explore charming lighthouses that offer a glimpse into the town's maritime heritage.
• Vineyards and Wineries: Discover local vineyards where you can enjoy tastings of exquisite wines amidst beautiful landscapes.
• Outdoor Activities: Engage in cycling, hiking, and fishing along scenic routes and tranquil waters.
• Cultural Experiences: Visit local museums and galleries that showcase Southold's rich history and artistic flair.

Popular types of accommodation in Southold

Your adventure in Southold, New York, awaits. Nestled on the picturesque North Fork, Southold boasts charming private homes, delightful cottages, and comfortable apartments for your stay. Explore local attractions such as the scenic beaches, historic lighthouses, and tranquil vineyards. Enjoy outdoor activities like cycling along the coastline or tasting fresh seafood at local eateries. Discover the perfect Southold rental that suits your needs and immerse yourself in this idyllic coastal town.

• Houses: The top choice for visitors in Southold, offering spacious and comfortable living spaces for families or groups.
• Cottages: Charming and quaint, these lovely retreats provide a cosy atmosphere, perfect for a romantic getaway.
• Apartments: Convenient and stylish, ideal for solo travellers or couples seeking a home away from home.
• Condos: Modern and well-equipped, perfect for those who enjoy amenities and community facilities.
• Villas: Luxurious and spacious, offering upscale living with stunning views for a lavish holiday experience.**

Top attractions in and around Southold

Southold, New York, offers a delightful blend of outdoor activities and cultural experiences perfect for a romantic getaway or an entertaining trip. Visitors can enjoy the picturesque beaches, explore lush urban parks, and delve into local history at its museums. This charming town caters to those seeking relaxation by the shore, immersive cultural encounters, and memorable outdoor adventures, making it an ideal destination for travellers looking to unwind and explore.

• Horton Lane Beach: A serene stretch of sand perfect for relaxation, offering stunning views and a tranquil atmosphere, ideal for sunbathing and swimming.
• Orient Point County Park: A family-friendly park featuring lush landscapes, picnic areas, and walking trails, perfect for outdoor activities and enjoying nature.
• Sag Harbor Marine Park: An adventurous marina where you can engage in various water sports, explore the beach, and soak in the vibrant marina atmosphere.

Things to do recommended for couples

Southold offers a charming escape for couples. Explore the serene vineyards with a wine tasting, stroll along the pristine beaches, or enjoy a scenic bike ride through the picturesque countryside. Don’t miss a sunset picnic by the water for a truly romantic evening.

Things to do recommended for families

Families will delight in the sandy shores of Southold's beautiful beaches, explore the interactive exhibits at the Southold Historical Society, or enjoy a fun day picking fresh fruit at local farms. Don't miss the charming shops and eateries that offer a taste of the area's unique culture.

Things to do recommended for groups

Experience the thrill of motor racing at Riverhead Raceway, located 29km from Southold. Gather your group for an adrenaline-fuelled day filled with sports and adventure vibes, perfect for creating unforgettable memories together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When travelling with a group, family, pets, or seeking longer stays, it's important to use filters that align with your specific needs. Here are some helpful booking tips for Vrbo.

• Traveling to Southold with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
• Traveling to Southold with young kids: Travelling with young children can indeed be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it would be wise to think about your closeness to family-friendly attractions.
• Taking your pets with you to Southold: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many 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 in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features such as a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic experiences, perfect for a memorable vacation. Visitors can explore the charming landscapes, indulge in family-friendly activities, and soak up the sunny weather. The town is rich in history and scenic beauty, making it an ideal destination for excursions. Whether you’re enjoying a leisurely stroll along Soundview Avenue or discovering the local wineries, Southold promises a captivating getaway for all travellers.

• Hamptons: Situated approximately 16km from Southold, the Hamptons are renowned for their stunning beaches and outdoor activities, making it a prime destination for those seeking a romantic escape. Visitors can indulge in golfing at exquisite courses or enjoy the snowy slopes during winter. Highlights include charming local beaches, family-friendly shores, and picturesque lakes that offer a serene backdrop for relaxation and recreation. Whether you're lounging on the beach or exploring quaint local shops, the Hamptons promise a delightful getaway.
• Greenport: Just 6km away from Southold, Greenport is a charming coastal town that captivates visitors with its outdoor allure and romantic ambiance. This delightful city offers a variety of activities, including access to golf courses and vibrant recreational areas, as well as an array of music concerts throughout the year. The local attractions, such as its beautiful beaches, family-friendly shores, and lush parks, provide ample opportunities for adventure and relaxation. Greenport's inviting waterfront and friendly atmosphere make it a must-visit destination.
• Sag Harbor: Located about 13km from Southold, Sag Harbor is an enchanting city with a rich maritime history that attracts outdoor enthusiasts and romantics alike. The area boasts excellent golf courses, scenic beaches, and tranquil lakes, perfect for a leisurely day out. Visitors can enjoy a variety of activities, from sunbathing on family beaches to exploring the surrounding natural beauty. With its quaint streets and vibrant arts scene, Sag Harbor offers a unique blend of relaxation and culture, making it an ideal spot for a memorable vacation.

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.

Booking with Vrbo is a breeze

Looking to enjoy savings on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant discounts. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your journeys, allowing you to easily create new trips, resume where you left off, and organise your existing plans. You can view your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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.