Southold vacation rentals

We found 988 vacation rentals — enter your dates for availability

Select from 116 homes, 13 cottages, and other vacation rentals in Southold to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Southold

Showing deals for:Sept 11 - Sept 18

Image gallery for Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

10% off
Price is CA $1,885
CA $16,934 total
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

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Find out more about Southold

Explore the waterfront setting in Southold

The area's wineries and monuments are just a few of the reasons to vacation in 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 hoping to discover things to do in the city? Venture out of your vacation home and experience everything that makes Southold a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Croteaux Vineyards (1.5 mi / 2.4 km)
  • 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)

Exploring the natural landscape of Southold

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Southold. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you'd prefer to travel by train, you can make your way to Southold Station.

Frequently asked questions

What is the best area to stay in Southold when booking a vacation rental?
When considering a vacation 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 vacation home in Southold?
Prices for vacation 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 travelling 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.
Are there any discounts for Southold vacation 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 vacation experience.
What is the most popular type of vacation rental accomodation in Southold?
In Southold, vacation houses are the predominant type of vacation 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 vacation 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 vacation 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 vacation home with a pool or hot tub in Southold?
In Southold, there are a variety of vacation 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. Find your rental in Southold with a pool or a hot tub.
Can I find long-stay vacation rentals in Southold?
A long-stay vacation 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 vacation 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 vacation rentals in Southold?
In Southold, New York, there is a substantial selection of remote work vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The peak season for visiting Southold typically runs from June to August, with July being the most popular month for vacation 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 vacation 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 vacation rental?
Book your Southold vacation 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 vacation 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 vacation 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 vacation 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.

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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