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Southold vacation rentals

We found 977 vacation rentals — enter your dates for availability

Select from 120 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:May 22 - May 29

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

9% off
Price is $1,136
$7,951 for 7 nights
All fees included
Renovated Farmhouse on Vineyard w/ Heated Pool, mins from Beach + Farm

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Find out more about Southold

Why visit Southold

  • Beautiful Beaches: Southold boasts stunning beaches perfect for relaxation and water activities.
  • Outdoor Adventures: Ideal for nature lovers, Southold offers various outdoor activities, from hiking to biking.
  • Rich History: Explore fascinating history museums and learn about the area's cultural heritage.
  • Charming Neighborhoods: Discover picturesque neighborhoods featuring luxury homes and scenic views.
  • Cozy Accommodations: Choose from a variety of vacation rentals, including charming cottages and stylish apartments.

Popular types of accommodation in Southold

Planning a getaway to Southold? You're in for a treat. This charming destination offers a variety of vacation rentals, including private homes, cozy cottages, and stylish apartments. Whether you're searching for spacious townhouse rentals or inviting houses, Southold has something for everyone. Explore the options and find the perfect Southampton home for rent to make your stay memorable.

  • Houses: The top choice for travelers in Southold, offering spacious and comfortable accommodations for families or groups seeking a home-like experience.
  • Cottages: A charming option, perfect for those wanting a cozy retreat surrounded by nature and local character.
  • Apartments: Ideal for solo travelers or couples, these rentals provide convenience and a taste of local living.
  • Condos: A popular choice for those looking for modern amenities and access to community features.
  • Villas: Luxurious spaces that offer a more upscale experience for those seeking relaxation and privacy.**

Top attractions near Southold

Southold, New York, is a fantastic destination for outdoor enthusiasts, couples, and those seeking entertainment. With a variety of attractions, including beautiful beaches, urban parks, and fascinating history museums, visitors can immerse themselves in the area's culture and natural beauty. Whether you're looking for a romantic getaway or an outdoor adventure, Southold offers something for everyone to enjoy during their vacation.

  • 67 Steps Beach: Located 5 miles from Southold, this beach offers a serene escape with its picturesque views and tranquil atmosphere. The unique 67 steps leading to the sandy shore enhance its charm, making it perfect for relaxation and sunbathing.
  • Railroad Museum of Long Island: Just 4 miles away, this museum showcases the rich history of railroads in the region. With engaging exhibits and historic trains, it offers a cultural experience for enthusiasts and families alike.
  • Sag Harbor Marine Park: Situated 8 miles from Southold, this marina provides an outdoor adventure with opportunities for kayaking, fishing, and picnicking. Its scenic waterfront and beach vibes make it a perfect spot for exploration.

Things to do recommended for couples

Experience romance in Southold with a visit to Pindar or Raphael Vineyards, both offering delightful wine tastings just 3 miles away. For a fun twist, head to Shelter Island Whale's Tail mini golf, only 5 miles away, perfect for a playful couple's outing.

Things to do recommended for families

Families can experience the charming Greenport Carousel just 4 miles away, unwind at Goldsmith's Inlet Park 3 miles away, or enjoy the thrilling rides at Splish Splash Water Park located 19 miles from Southold. Each spot offers unique fun and relaxation for all ages.

Things to do recommended for groups

Explore the Greenport Farmers' Market for local produce, tee off at Noyac Golf Club for a fun day outdoors, and catch a show at Bay Street Theatre for a memorable evening filled with culture and entertainment. These experiences promise a fantastic group getaway in Southold.

*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

If you're planning a trip with a group, traveling with family, bringing your pets along, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful tips for booking on 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 areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Southold with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Southold: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate, explore Vrbo listings 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 vacation rentals offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Southold

Southold offers a charming escape with its serene surroundings and outdoor activities perfect for romantic getaways or family adventures. Explore the nearby neighborhoods, where luxury homes and picturesque scenery await. Experience the rich history and vibrant atmosphere of New York’s North Fork, with its family-friendly attractions and exquisite excursions. Whether you're looking for a vacation home or just a peaceful retreat, Southold promises an unforgettable experience.

  • Hamptons: Located approximately 10 miles from Southold, the Hamptons are renowned for their stunning beaches and outdoor activities, making it a prime destination for romantic getaways. Visitors can indulge in a round of golf, attend music concerts, or relax at luxurious resorts. The beautiful beaches, including family-friendly spots and serene lakes, offer ideal settings for sunbathing, swimming, and picnicking, ensuring a memorable coastal experience.
  • Greenport: Just 4 miles from Southold, Greenport is a charming city known for its outdoor adventures and romantic atmosphere. The waterfront town features a variety of activities, from golfing to live music events. Visitors can explore picturesque beaches, family-friendly shores, and event venues that host conferences and gatherings. Greenport's vibrant maritime history and local eateries provide a delightful experience for tourists seeking a blend of relaxation and entertainment.
  • Sag Harbor: Situated about 8 miles from Southold, Sag Harbor captures the essence of seaside charm with its outdoor activities and beautiful beaches. This historic city is perfect for romantic excursions, featuring golf courses and nearby ski fields for winter enthusiasts. Local attractions include serene beaches, family-friendly areas, and lovely parks, making Sag Harbor a fantastic spot for both relaxation and recreation. Enjoy the picturesque views and warm community vibe as you explore this delightful destination.

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 money on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of even greater savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your trip.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly area to plan new trips, continue your previous arrangements, or manage your travel itinerary. You'll easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • 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 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)
  • Meschutt Beach (12.4 mi / 19.9 km)
  • LongHouse Reserve (13.1 mi / 21.1 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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Southold, New York, a popular area to stay is along the scenic North Fork, particularly in neighborhoods such as Mattituck and Cutchogue. These charming communities offer a delightful mix of coastal beauty and local attractions.

In Mattituck, you'll find stunning waterfront views and easy access to beautiful beaches, making it superb for those looking to enjoy a relaxing getaway. The area is also home to some fantastic vineyards, where you can indulge in wine tastings and explore the picturesque landscapes. One of the top attractions here is the Mattituck Beach, a lovely spot for sunbathing or enjoying a picnic.

Cutchogue, on the other hand, is known for its quaint, small-town feel and is surrounded by lush farmland and vineyards. This area is great for those who appreciate outdoor activities, with opportunities for hiking and visiting local farms. A highlight of Cutchogue is the Cutchogue Village, which offers charming shops and eateries that capture the essence of the North Fork's agricultural heritage.

Both neighborhoods have a variety of vacation rental options, ranging from cozy cottages to spacious homes, ensuring visitors can find a superb place to stay while enjoying all that Southold has to offer.
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 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 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 offers picturesque seaside options. The neighborhoods near Southold Bay are particularly appealing, as they provide access to serene beaches and stunning sunset views. Many vacation rentals here feature amenities such as spacious decks, outdoor grills, and private beach access, making them superb for families or groups looking for a relaxing getaway.

Additionally, the vicinity around Hashamomuck Pond offers charming cottages and bungalows that often come with kayaks or paddleboards for exploring the calm waters. These properties may also include fully equipped kitchens and cozy living areas, ideal for gatherings after a day spent at the beach. The local area is dotted with wineries and farm stands, adding a unique touch to the beach experience, with many rentals being conveniently located near these attractions.

For those who enjoy a mix of beach and nature, the nearby Orient State Park features hiking trails and picnic areas, and some rentals in the area may provide easy access to these outdoor spaces.
What is the most popular type of vacation rental accomodation in Southold?
In Southold, vacation houses are the most popular type of rental, with approximately 93 available throughout the area. These houses are often situated near the scenic shores of Long Island Sound and are ideal for families or groups looking for ample space. Most vacation houses come equipped with multiple bedrooms, fully stocked kitchens, and outdoor spaces such as decks or patios for enjoying the fresh coastal air. Additionally, there are about 12 cottages that offer a charming, cozy alternative, often featuring rustic decor and proximity to local beaches and vineyards.
Are there any family house rentals in Southold?
In Southold, New York, there is a substantial selection of family-friendly vacation rentals, with around 80 homes available throughout the area. This charming locale, situated on the North Fork of Long Island, is ideal for families seeking both relaxation and adventure. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor patios or decks that are great for family gatherings.

Visitors can enjoy amenities such as private yards, barbecues, and sometimes even access to nearby beaches or community parks. The area is known for its beautiful vineyards, scenic waterfronts, and local farms, offering plenty of opportunities for family outings.
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 32 options to choose from. This picturesque town on Long Island's North Fork is known for its beautiful vineyards and charming coastal scenery. Travelers can find properties in various neighborhoods, including those near the waterfront, where rentals often boast private pools, hot tubs, and expansive outdoor areas superb for relaxation and entertaining. Many of these homes come equipped with modern amenities such as fully stocked kitchens, spacious living rooms, and outdoor dining spaces, allowing guests to enjoy both comfort and luxury during their stay.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Southold?
In Southold, there are numerous pet-friendly house rentals available, offering a variety of accommodations for travelers. Many of these properties provide amenities such as spacious yards, outdoor decks, and fully equipped kitchens, making them ideal for families or groups traveling with pets.

The Southold area is known for its beautiful beaches and proximity to nature, providing ample opportunities for outdoor activities with pets. Nearby points of interest include the scenic Southold Town Beach and the picturesque beaches along the North Fork. Additionally, the local vineyards and farms often welcome pets, offering a great experience for pet owners looking to enjoy the area's charm.
Are there any remote work vacation rentals in Southold?
In Southold, New York, there are numerous remote work vacation rentals available, with around 98 options to choose from. The area is known for its serene landscapes, charming vineyards, and proximity to picturesque beaches, making it an ideal setting for working remotely while enjoying a getaway. Many properties offer essential amenities for remote work, including high-speed internet, dedicated workspace with desks and chairs, and free Wi-Fi in the rental units.

Travelers can expect a variety of accommodations, ranging from cozy cottages to spacious homes, often featuring outdoor spaces where you can take breaks and relax in nature. Additionally, Southold's location on the North Fork provides easy access to local attractions such as wineries, farm stands, and beautiful waterfront views, enhancing the overall experience for those balancing 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 travelers 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 kitchens, which allow travelers to prepare their own meals during their stay. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the beautiful surroundings. Fireplaces are common, adding a cozy touch for those cooler evenings. Additionally, rentals often come equipped with blenders for making smoothies or cocktails, and onsite parking is typically available for convenience.
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 peak summer months of June through August, with July being particularly popular among travelers. This vibrant season attracts families and beach enthusiasts eager to soak up the sun along the beautiful North Fork beaches. With warm temperatures typically ranging from the mid-70s to low 80s Fahrenheit, it's an ideal time for outdoor activities such as swimming, kayaking, and exploring local vineyards.

During July, the atmosphere in Southold is lively, filled with events like farmers' markets, outdoor concerts, and charming festivals that highlight the region's rich culture and community spirit. This season not only offers pleasant weather for beach days but also an array of nearby attractions, ensuring you have plenty of opportunities for sightseeing and relaxation.

For those seeking a more budget-friendly option, consider visiting in December. While this month falls outside of the main tourist season, it offers a unique charm with its peaceful winter landscapes and festive holiday events. It's a great time to enjoy quiet walks along the shoreline, sample local cuisine, and appreciate the slower pace of life in Southold.
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, New York, United States of America?
In Southold, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque beaches along the Long Island Sound, such as Horton Point Beach and Southold Town Beach, offer opportunities for swimming, sunbathing, and scenic walks. The nearby Southold Historical Society Museum showcases the rich history of the region, featuring exhibits and artifacts that reflect its maritime heritage.

Wine enthusiasts can explore the numerous vineyards and wineries in the North Fork region, with many located just a short drive away, offering tastings and tours in a beautiful setting. The charming downtown area features boutique shops and local eateries, great for experiencing the local cuisine and shopping for unique souvenirs.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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