Southold holiday rentals

We found 965 holiday rentals — enter your dates for availability
Select from 117 homes, 12 cottages and other holiday rentals in Southold to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Southold

Showing deals for:18 Dec - 25 Dec

Dining
Living area
Living area
Pool
Exceptional
(12 reviews)

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

Orient

8% off
AU$17,025
for 7 nights, 1 room
AU$2,432 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Private kitchen
Exterior
Outdoor dining
Interior
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
AU$6,090
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Master bedroom with ensuite bathroom
Pool
Outdoor dining
Exterior
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,057
for 7 nights, 1 home
AU$1,722 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Living area
Living area
Property grounds
Private kitchen
Exceptional
(29 reviews)

Incredible Beachfront Home w/ Private Beach!

Mattituck

7% off
AU$5,193
for 7 nights, 1 cottage
AU$742 per night
includes taxes & fees
Incredible Beachfront Home w/ Private Beach!
Living area
Outdoor dining
Exterior
More vineyard views
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,795
for 7 nights, 1 home
AU$1,399 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Large Dining/Kitchen Space
Exterior
Spacious Main Floor Living room
Pool
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
AU$12,821
for 7 nights, 1 home
AU$1,832 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Dining room from kitchen
Master bed onto balcony
Kitchen from dining room
Hall into sitting room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$19,100
for 7 nights, 1 home
AU$2,729 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Outdoor dining
Dining
Private kitchen
Living area
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$6,937
for 7 nights, 1 cottage
AU$991 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Stairs to the upstairs living room, kitchen and dining room
Pool
Terrace/patio
Living room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
AU$11,367
for 7 nights, 1 home
AU$1,624 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Interior
Terrace/patio
Private kitchen
Dining
Exceptional
(19 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
AU$6,715
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Interior
Property grounds
Living area
Room
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off
AU$4,144
for 7 nights, 1 home
AU$592 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
The front porch
A view of the house and pool from the creek, looking south
The kitchen is all glass with a spectacular view of the pool and creek
The front of the house
Exceptional
(20 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,243
for 7 nights, 1 home
AU$892 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Dining
Private kitchen
Room
Private kitchen
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
AU$6,409
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Bathroom 1- upstairs
Dining
Private kitchen
Den/ play room has a sofa with queen sized pullout sofa
Exceptional
(13 reviews)

Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!

Riverhead

8% off
AU$8,622
for 7 nights, 1 home
AU$1,232 per night
includes taxes & fees
Renovated Farmhouse on Vineyard-Heated Pool + mins from Beach + Walk to Harbes!
Living Room
Kitchen
Room
Exterior
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,820
for 7 nights, 1 home
AU$689 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Morning breakfast room
Every season brings special flower blooms
Second living room once called the "parlour"
Our porch is furnished with plants for a Gilded Age feel
Exceptional
(37 reviews)

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport

12% off
AU$10,943
for 7 nights, 1 home
AU$1,563 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Interior
Pool
Dining
Private kitchen
Wonderful
(20 reviews)

2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub

Riverhead

8% off
AU$6,003
for 7 nights, 1 home
AU$858 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
Kitchen Fireplace Eat In Kitchen & in the next photo includes new kitchen table
Crushpad of Charming Boutique vineyard nearby- Rosehill
8 Hands Farm
Exceptional
(30 reviews)

North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk

Laurel

26% off
AU$3,411
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
North Fork Ranch Home in Wine Country with Pool- 2 Beaches 5 Min Walk
Interior
Private kitchen
Room
Outdoor dining
Exceptional
(15 reviews)

Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.

Jamesport

16% off
AU$8,316
for 7 nights, 1 home
AU$1,188 per night
includes taxes & fees
Newly renovated 4-bedroom farmhouse on beautiful vineyard - Great location.
Dining
Outdoor dining
Exterior
Private kitchen
Exceptional
(7 reviews)

Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.

Shelter Island

7% off
AU$1,959
for 7 nights, 1 home
AU$280 per night
includes taxes & fees
Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
Shed
Kitchen
Exterior
Living Room
Exceptional
(107 reviews)

Relax in this light-filled home, steps from the beach and a short walk to town!

Greenport

8% off
AU$6,050
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Lovely pond front cottage on the North Fork.
View from main living area
Comfortable living room with gas fireplace for ambiance in colder months.
Wonderful screened in porch for enjoying the sights and sounds of nature .
Exceptional
(32 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold

8% off
AU$3,193
for 7 nights, 1 cottage
AU$456 per night
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country
Property grounds
Property grounds
Interior
Pool
Exceptional
(88 reviews)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

8% off
AU$4,854
for 7 nights, 1 apartment
AU$693 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Living area
Pool
Private kitchen
Terrace/patio
Exceptional
(11 reviews)

Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport

East Marion

8% off
AU$8,860
for 7 nights, 1 home
AU$1,266 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport

  • 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, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the waterfront setting in Southold

The area's wineries and monuments are just some of the reasons to come on holiday to 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 looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southold a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 appreciate the scenery, Southold is a great spot to appreciate mother nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you prefer train travel, the main station is Southold Station.

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.
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.
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 Stayz.
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.
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.
Are all fees included in the Southold holiday homes prices shown on Stayz?
Stayz 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.
Are there any Southold holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Southold holiday homes?
You can find great discounts on holiday homes in Southold on Stayz, 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.
Can I change or cancel my Southold holiday home booking on Stayz?
To find Southold holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Southold?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Southold holiday home?
Book your Southold holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Southold?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Southold to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas