Photo by Benny Goh

Southold vacation rentals

We found 979 vacation rentals — enter your dates for availability

Select from 118 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.

Vacation rentals with weekly discounts - Southold

Showing deals for:Mar 27 - Apr 3

Image gallery for Lovely Cottage in the Heart of Long Island Wine country

Lovely pond front cottage on the North Fork.
9.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold

10% off
Price is CA $338
CA $3,079 total
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country

Find spaces that suit your style

  • 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, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • Shinn Estate Vineyards (6.6 mi / 10.6 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:

  • 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)
  • LongHouse Reserve (13.1 mi / 21.1 km)
  • Cooper's Beach (14 mi / 22.5 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 charming neighbourhood of New Suffolk is often regarded as a popular area to stay. This quaint community is situated along the picturesque shores of the Peconic Bay, offering stunning waterfront views and a relaxed, laid-back atmosphere. Visitors to New Suffolk can enjoy the nearby New Suffolk Beach, which is great for a leisurely day of sunbathing or swimming. Additionally, the area is known for its proximity to various vineyards and wineries, making it an ideal spot for those looking to indulge in local tastings and tours.

Another appealing option is the Southold Village area, where guests can experience firsthand the local culture. This neighbourhood boasts a lovely selection of shops, eateries, and art galleries, providing plenty of opportunities to explore the vibrant community. The Southold Historical Society is a highlight in this area, offering insight into the rich history and heritage of the region.
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, New York, the area around Southold Bay is particularly appealing. This picturesque stretch offers easy access to sandy beaches and stunning views of the bay, making it an excellent choice for travellers seeking a relaxing seaside getaway. Many properties in this area come with amenities such as spacious decks for outdoor dining, private beach access, and fully equipped kitchens, great for families or groups wishing to enjoy a home-cooked meal after a day in the sun.

Another great option is the vicinity of the North Fork, especially near the beaches at Horton Point and Founders Landing Park. Here, you can find charming beach houses that often boast features like outdoor showers, fire pits, and landscaped gardens. These rentals provide an inclusive setting for enjoying summer evenings while being close to local attractions such as vineyards and farm stands that the North Fork is famous for.

Additionally, the area around the Long Island Sound is worth considering. Properties here typically offer stunning waterfront views and direct access to the beach, with many featuring amenities like large patios, private docks for boating enthusiasts, and ample parking for guests. The proximity to local restaurants and shops adds to the convenience, allowing travellers to fully immerse themselves in the laid-back coastal lifestyle.
What is the most popular type of vacation rental accomodation in Southold?
In Southold, vacation houses are the most popular type of accommodation, with around 100 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups looking to enjoy the serene surroundings. Additionally, there are about 13 cottages which offer a charming and quaint experience, often equipped with cosy living areas and kitchen facilities for a more intimate stay. Several apartments can also be found, providing a convenient option for couples or solo travellers seeking a more compact living space while still enjoying the local attractions.
Are there any family house rentals in Southold?
In Southold, New York, there are numerous family-friendly house rentals—specifically around 86 available options. This charming town on the North Fork of Long Island is an excellent choice for families looking to enjoy a coastal getaway. Many of these properties boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for children to play and explore.
Can I rent a vacation home with a pool or hot tub in Southold?
In Southold, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 35 options to choose from. This charming town, located on Long Island's North Fork, offers a tranquil escape while being close to beautiful beaches and local wineries. Many of the properties come with enticing amenities such as private pools, hot tubs, outdoor patios, and spacious gardens, great for relaxation and family gatherings. 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 properties boast amenities such as spacious backyards, fully equipped kitchens, and outdoor seating areas, great for enjoying the pleasant coastal weather.
Are there any remote work vacation rentals in Southold?
In Southold, New York, there is a robust selection of remote work-friendly vacation rentals, with around 103 available options. Many of these properties are equipped with essential amenities for working remotely, including high-speed Wi-Fi, dedicated office spaces, and comfortable desks with chairs. Some rentals even feature additional conveniences such as computer monitors and safe spaces for securing valuables, ensuring a productive work environment. 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 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 vacation rentals come with private patios, providing outdoor spaces to relax and enjoy the pleasant surroundings.
When is the best time to visit Southold for a vacation rental?
The best time to visit Southold for a vacation rental is during the summer months, particularly in July, when the area is buzzing with activity. This peak season, which spans from June to August, offers visitors the chance to indulge in a wide array of outdoor experiences, such as beach outings, wine tastings, and leisurely bike rides along scenic coastal paths. With temperatures typically hovering in the mid-20s Celsius, the warm weather invites travellers to enjoy the picturesque beaches and charming local attractions.

July stands out as the most popular month, drawing families and groups eager to soak up the sun and embrace the vibrant community spirit. The atmosphere is lively, with farmers' markets, local festivals, and the chance to sample fresh seafood at waterfront restaurants. Whether relaxing on the beach or exploring the nearby vineyards, there's something for everyone during this peak season.

For those seeking a quieter and more budget-friendly experience, consider visiting in December. While the weather is cooler, typically around 5 to 10 degrees Celsius, this month offers a serene charm, with fewer crowds and the opportunity to enjoy the area's natural beauty in a more tranquil setting. Exploring the winter landscapes and participating in local vacation festivities can be a delightful alternative.
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 area's natural beauty and local culture. The charming village of Southold is dotted with historic sites, including the Southold Historical Society's museum, which offers insights into the town's rich maritime history. Nearby, the picturesque vineyards of the North Fork provide opportunities for wine tasting and tours, with several wineries featuring scenic views and outdoor seating areas.
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.

More Vacation Ideas