Southold vacation rentals

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Select from 122 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:Dec 19 - Dec 26

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Outdoor dining
10 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Peconic River Boatel

Riverhead, NY

9% off
Price is $445
$3,118 for 7 nights
All fees included
Peconic River Boatel

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Find out more about Southold

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)
  • Noyac Golf Club (6.5 mi / 10.4 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 planning a vacation rental in Southold, New York, the best area to consider is the picturesque North Fork, known for its charming coastal atmosphere and scenic vineyards. This region offers a variety of properties, with many vacation rentals situated near the waterfront and located among the lush landscapes.

One particularly appealing neighborhood is the Southold Village area, which provides easy access to the beautiful beaches, such as Southold Town Beach, where you can enjoy sunbathing or swimming. Additionally, the nearby Southold Historical Society offers a glimpse into the rich history of the region, superb for those who appreciate cultural experiences.

Another fantastic option is the area around Mattituck, which is renowned for its wineries and farm stands. Here, you can explore the stunning vineyards and enjoy wine tastings at some of the local wineries, making it an ideal spot for wine enthusiasts. The Mattituck Creek is also great for kayaking and paddleboarding, providing an adventure for those looking to explore the natural beauty of the area.

Overall, the North Fork of Southold boasts a range of vacation rentals, offering visitors a superb blend of relaxation, outdoor activities, and local charm.
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, New York, consider the picturesque waterfront areas along the north fork of Long Island. The beaches near Southold's town center, especially around the scenic shores of Peconic Bay, offer a selection of vacation rentals that provide stunning views and easy access to the water. Many of these properties come with amenities such as outdoor decks, barbecue grills, and spacious living areas that are great for families or groups looking to enjoy the beach lifestyle.

The area around Founders Landing Park is particularly appealing, with beach houses that often feature private paths to the sandy shore, outdoor showers, and fire pits for evening gatherings. Additionally, the nearby Southold Town Beach provides a family-friendly atmosphere, and rentals in this area typically include modern kitchens and access to local markets for fresh seafood and produce.

Travelers can also explore the charming community of New Suffolk, which offers a quaint village feel and proximity to both the bay and the Long Island Sound. Many rentals here have unique character, with some converted from historic structures, and often come equipped with amenities like kayaks or bicycles for exploring the surrounding areas. Find your rental near the beach in Southold.
What is the most popular type of vacation rental accomodation in Southold?
In Southold, vacation houses are the most popular type of rental, with around 104 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing getaway. Many of these properties also come with outdoor spaces, such as decks or gardens, allowing guests to soak in the beautiful surroundings. Additionally, there are about 13 cottages, which offer a charming and cozy atmosphere, superb for a more intimate stay.
Are there any family house rentals in Southold?
In Southold, New York, there is a wide selection of family-friendly vacation rentals available, with around 87 options to choose from. This charming area, located on Long Island's North Fork, offers a delightful mix of coastal beauty and local attractions. Many homes in the vicinity feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy the fresh air.

Travelers can find properties with amenities such as private gardens, decks for family barbecues, and even access to nearby beaches, great for a fun day in the sun. Visitors to Southold can also explore local points of interest like the Southold Historical Society, which provides insight into the area's rich history, or take a short drive to nearby vineyards for a family outing. See all family-friendly rentals in Southold.
Can I rent a vacation home with a pool or hot tub in Southold?
In Southold, there are many vacation homes available for rent that feature pools and hot tubs, with approximately 35 options to choose from. This picturesque area on Long Island's North Fork is known for its scenic vineyards, beautiful beaches, and charming small-town atmosphere. Travelers can find properties in various neighborhoods, including those near the waterfront, which offer stunning views and easy access to the beach.

Rentals in Southold typically come equipped with desirable amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, making them ideal for families and groups seeking relaxation and entertainment. Many homes also have outdoor dining areas and barbecue grills, great for enjoying the pleasant weather. 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. 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, travelers will find a variety of pet-friendly house rentals, with around 55 options available. Many of these homes are situated close to the picturesque beaches and waterfront areas, providing easy access for pet owners to enjoy leisurely walks along the shore. The rentals typically offer amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, making them great for families or groups traveling with pets.

The town features several parks and natural spaces, including the beautiful Southold Town Beach, which is a great spot for pets to enjoy the outdoors. Additionally, the nearby Orient Beach State Park offers scenic views and trails ideal for walking pets. See all pet-friendly rentals in Southold.
Are there any remote work vacation rentals in Southold?
In Southold, New York, there are numerous remote work vacation rentals available, with around 97 options to choose from. This charming coastal town is situated on the North Fork of Long Island and offers a serene environment for working remotely. Many properties in the area come equipped with essential amenities for remote work, including Wi-Fi, dedicated office spaces, and comfortable workstations with desks and ergonomic chairs.

Travelers can expect accommodations that provide a peaceful atmosphere conducive to productivity, often featuring additional amenities such as computer monitors and safety deposit boxes for added convenience. The proximity to beautiful beaches, local wineries, and scenic views of the Long Island Sound makes Southold an appealing choice for those looking to balance 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 WiFi, which allows travelers to stay connected during their stay. Most rentals also feature kitchens, enabling guests to prepare their own meals and enjoy home-cooked dining. Many properties come equipped with a blender, superb for making smoothies or cocktails, and a coffee/tea maker to start the day with a warm beverage. Additionally, patios are common, providing outdoor spaces for guests to relax and enjoy the scenic views of this charming coastal town.
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 comes alive with vibrant energy and delightful opportunities. This peak season, spanning from June to August, offers warm weather ideal for outdoor activities such as beach outings, wine tastings, and exploring the beautiful North Fork vineyards. Travelers can expect daytime temperatures ranging from the mid-70s to low 80s Fahrenheit, great for enjoying the region's picturesque landscapes.

July is especially popular among vacationers, as visitors flock to Southold to take advantage of the thriving local scene. You can indulge in leisurely days at the beach, savor fresh seafood at local restaurants, or participate in various festivals and events that celebrate the area's rich culture.

For those looking for a more budget-friendly experience, consider planning your trip in December. Although this month falls within the low season, it provides a unique opportunity to enjoy the charm of Southold during the quieter winter months.
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 enjoy a variety of attractions that highlight the area's natural beauty and local culture. The charming village of Southold is known for its picturesque waterfront, where travelers can explore the scenic beaches such as Southold Town Beach and Horton Point Park, offering stunning views of the Long Island Sound.

Wine enthusiasts will appreciate the nearby North Fork Wine Region, dotted with numerous vineyards and tasting rooms, making it an ideal destination for a leisurely afternoon of wine tasting. Additionally, the historic village features several quaint shops and eateries, superb for a relaxing day out.

For those interested in history, the Southold Historical Society offers insights into the area's past, with preserved buildings and exhibitions. Nature lovers can also visit the nearby Orient Beach State Park, which features hiking trails and opportunities for birdwatching along the coastline.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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